#8: Rick Nucci, Guru

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 8, and I'm thrilled to welcome Rick Nucci to the show. Rick's the co-founder and CEO of Guru. We have this incredible conversation where we talk about the importance of having complementary founder skills, and he's very open about the dark days of his breakup with his co-founder at his first company. Now, as you'll hear, when Rick talks about culture and rituals, he just lights up, and we get into his philosophy about culture as well as specifically how Guru uses it in hiring. Rick also talks about how he's learned what to do when he doesn't know what to do and why he forces people to vent. Please enjoy this incredible conversation with Rick Nucci. Rick Nucci is the co-founder and CEO at Guru. Guru's mission is to give every team in the world trusted information so they can do their best work. Prior to Guru, Rick was the founder and chief technology officer of Boomi. Boomie was acquired by Dell in 2010. Rick is also a proud and active member of the Philadelphia startup community. And I wanna thank Jake Stein, another patriotic Philly serial entrepreneur, for introducing us. And so Rick, welcome to the show.

Thank you. What a lovely lead-in. I appreciate it. Happy to be here.

I'm so happy to have you. And I just wanna jump right in with a quote on your Twitter profile. And so of all places, I mean, Twitter is like the place of record. "Success is not a license for arrogance," you say.

Yes.

And of course I agree. Why does that sentence resonate with you and why of all places do you have to throw that on Twitter?

Well, why it resonates with me is I think I'll frame it in maybe a positive light, which is— Yeah. I tend to admire people twice as much when they have achieved something remarkable and the way they show up and the way they engage with people around them. It could be their team, it could be customers, it could be a community. When they show up with a sense of humility and a sense of vulnerability, I just have so much admiration for that because I think that is perhaps a leadership trait that is Certainly in the top 3. And so I put it on Twitter because it tends to be a bit of a signal of like, I don't really have any interest in spending time with sort of the contrary to that. And I think there's, you know, and it's actually a company value of ours, you know, I think it can often be associated with people who tend to take themselves too seriously. And that just tends to be a behavior style that isn't really compatible with me.

Did you come up with that quote or did you take that from somebody?

I think I did. I think I did. I don't remember reading it anywhere, so I'll— but I maybe should Google that and see if that's true. But I think it is.

Well, maybe it's you. Maybe it's you. I love that because I think it's sort of philosophy in this compact sentence. I think that's beautiful. So when you started Boomy, when you started, I guess, your entrepreneurial journey, you were 24 years old. So that was maybe a couple of years ago. And, and I guess I would ask you as a starting point, like what things, what are some things you learned from leadership, like from trial and error from that experience?

Yeah. So, so many things. Um, I think maybe to share two that are probably, um, focused on kind of the founding team, that initial team, uh, I would say first, learned the hard way, a.k.a. didn't do this and made a mistake, was what I now feel to be pretty important, which is complementary founder skills. And so I think that one way to walk into a company together with at least one other founder, if that's the journey you're on, is to have that honest conversation upfront and say, hey, what do we— what do we respectively think our skills are that we're bringing to the table to start this thing? And, you know, at Boomi, we were sort of all varying kinds of technical people. And that led to some pretty, I think, real gaps in how we were, you know, at the earliest, earliest days of the company starting and building it that we, you know, again, through sort of hard knocks had to kind of figure out and adjust and make up for. And then I think the other big one that just led, you know, for us to so many problems in the early days was we kind of had this like grandiose, like, yeah, there was 3 of us, you know, oh, you know, we'll sort of, we'll make all decisions together and we'll just sort sort of talk it through. And that's such a, you know, that was such a disaster. I think like, first of all, like disagreement's actually really good. I think it's actually really healthy and normal. And, and sort of my biggest learning is, and I won't even call it a title, I think oftentimes this becomes a CEO, but you just need the tiebreaker. You, you need, you need to have the clarity around, hey, we're going to disagree on things, but we need a path forward. The, the, the, the, the, like guaranteed, you know, problem is if we don't actually make a decision or we just spend so much time internally, whatever, arguing or whatever. So I think that upfront conversation, I remember having that with Mitch, who's my co-founder at Guru, having that conversation with him way back in the beginning before we actually started about that. And I think we just got on the same page and kind of never looked back. And it was really just something that I just learned through pain, I guess.

Yeah, unfortunately, sometimes the best teacher. When you did sit down with Mitch, so I have sort of a tool that I call the co-founder prenup, the idea of bringing together, bringing both people together and really talking through your values and your skills and then also your vision for the future. What did you and Mitch talk about for Guru in advance that then helped you realize this was the right co-founder for you?

Uh, yeah, great question. I love that. I mean, I think the unfair part of that is I had already been working with Mitch actually for a long time. Uh, let's see. Yeah, probably by that point we had been— you know, he was, he was the first, you know, what I would call professional engineer that we hired at Boomi and eventually went on and ran all of engineering at Boomi and then left and started Guru with me. And so so much of that we had kind of naturally figured out in terms of how we complemented each other. Um, and, and so I think we sort of had that going in. I mean, you know, we have through several sort of like occasions and, and products been, been, been able to go and learn through the idea of like coming up with ideas for new products, bringing them to life. And, you know, Mitch is, is very much, you know, one of his greatest skills is he's technical but also respects and understands the need for, you know, execution and business outcomes and really can marry those two things together really well. And I think I can tend to complement that with coming up with a vision or a new product idea or evangelizing it, maybe getting other people excited about it. So we sort of, I think, had that conversation going in. But I, you know, I love the word prenup because I think the other areas where we did spend time was For example, equity, you know, for us, we had just sort of made the decision from the beginning and I had sort of brought it up with him from the beginning. Like equity is just 50/50. I think like there's lots of opinions on this. I think for me, you know, whatever it's been now, 7 years, like it's just never been a conversation ever, ever about equity between the two of us. And I think, you know, even if it's like one point here or one point there, it can— it cannot be the case. And I just sort of am happy that that's been there. And I think the other thing we both committed to out of the gate was a 4-year vesting period for our founding shares. Another thing that, you know, those— that, that's, you know, a few years ago now. But again, like, hey, things happen, right? If one of us had— and again, I lived through this— we didn't have founder, you know, 4-year vesting at Boomi, lived through the pain of that reality and the downsides of not doing that. So sort of setting that out of the gate this time, again, just simplifying life. And so I remember focusing on those things. I remember I remember, but I think a lot of the way we worked together was borne out through just like going through it already, which was a huge, you know, I feel very fortunate that that was able to happen.

Yeah, because you got to know each other without having to sort of ask these specific questions. You kind of already knew some of the answers.

Yes, exactly.

So I appreciate hearing that, and I definitely want to hear more about Guru, but I feel like I'd be remiss in not going back to Bhumi for one last question because I believe, and tell us the story, I believe that your other co-founders left the company and that there was, you know, sort of a brouhaha. And in some ways you kind of reformed the company. And I'll just tell you that the founders I work with very often, they get upset if their employees leave, to say nothing of their co-founders. So what happened and how did you process that? And then how did you sort of carry on after that?

Yeah, those were definitely dark days. I think, you know, I would say in terms of what happened there, there just emerged, I think, some pretty real differences of what we should be doing as a company pretty foundationally. And I think ultimately it manifested in, uh, one of the co-founders leaving, where, you know, myself and other members of the leadership team had a pretty aligned point of view that was not shared. And so, so, you know, we sort of made the really tough choice to kind of part ways. Um, but there were definitely times when I remember like considering leaving and it was not because I didn't believe in the company or the opportunity. It was, it was very much a, you know, hey, there's a personal, there's a maximum personal limit to some of this shit. We're spending so much time, you know, having this internal conflict and not focused on actually building the company and building the product and making customers successful and all those things that, that, that I almost threw up my hands and I didn't. Of course, very glad that I didn't. And I think some of the takeaways, I think a takeaway I'll share that you talked about employees leaving. And I actually think one of the things that we got lucky on, or I think maybe put a lot of energy into, was being very transparent with the team. I mean, at this time we were, I don't know, under 20 employees, and we're all sitting in one office together. So, you know, they know what's going on. Yeah, they know that things are not well, right, between the co-founders. They're not— they're highly intelligent people. Um, it's not— it's not— there's no benefit in trying to obfuscate away what's going on. And so we actually took, took the path of the opposite, right, which is just, just, you know, I remember sitting down with, with the key people on the team and just telling them in pretty direct detail, you know, what was going on and what I was planning to do about it. And of course, this is after I had, I had crossed over the like, oh, maybe I should just leave. I sort of back and, and sort of like fired up and bought into like figuring this out. And, and I think that transparency did help build trust. I think it did help those early employees go, okay, well, I understand what's happening. I think when, when, when it's obfuscated away or there's, there's, there's nothing being shared, everyone's going to write their own narrative. Right. And so, and so, so, so because we, because we were, you know, I think got in front of that and were proactive and shared what was going on. It was stressful. I think we— the downside is we put these early employees on that emotional roller coaster with us, like, what's going on, you know? But I think that's still way better than not saying anything and they get freaked out and maybe leave. And that likely would have been game over with some of the key people we had at the time at the company. So that didn't happen. I think I really learn to value, you know, the, the idea of transparency, the importance of internal comms, even when it's a small team of that size. And then turning that into once we had sort of, you know, you know, settled down the team, and we had sort of parted ways with the co-founder, you know, then focusing on the future, right, defining the vision, evangelizing it, carving a path forward for the team. And of course, this was the beginning of what became the, uh, as you described Boomi, the integration platform as a service that, that Boomi is known for today. At the time, it was, it was very much a, hey, this is a bet we're gonna make, um, like a burn the ships kind of bet we're gonna make. I mean, there's really no going back if we get this wrong, but, you know, we just believe in this opportunity. And that was sort of the beginning, I think, of the emergence of, you know, what, what became a really great, um, company. But yeah, dark, dark days for, for a while. The first 2 years were rough, um, yeah, to say place.

Yeah, that's really difficult. I guess I'm curious, like, what did you actually say to the team? Like, what, what words did you use to tell the team what was going on?

Uh, that there were very real and very, uh, potentially unrepairable problems between myself and the other co-founder at, at Boomi. And irreparable means, like, you know, this might not work. And, you know, this is— there's sort of some core misalignment around what's going on at the company. I am, you know, I very much believe X and Y, and here's why. And, you know, you said specifically X and Y was a lot I was saying around the vision and the future of the company and how we should be repositioning and how we should be, you know, what market we should be trying to go after, what product we should be building at a high level. And, and, you know, I just don't know if we're going to get there, you know, and what I mean by not going to get there is like not going to get there together, right? Meaning like, you know, one of us might not be here. Right. And so, so, so, you know, I'd say that was probably, you know, not a huge amount of time, but certainly months of time while that played out and eventually landed in, you know, us parting ways.

Right.

But, but yeah, so I mean, that, that kind of, of like, this is the situation, you know, kind of, kind of moment and an opportunity and just directness. And I think I've never actually asked those early team members what they thought about all that. Maybe, maybe it was just a huge stress to them, but I would hope that they would have valued, you know, that they valued the, the openness that, that we were sharing it, that we were sharing the reality of situation and we weren't trying to, you know, hand wave it or spin it or any of that stuff.

Right, or pretend it was different. And to your point, people are walking around and they're sensing the tension and they're feeling the tension and everyone's, "No, no, we're fine. Mommy and Daddy are fine." Right? Yes.

Exactly. Yeah.

So I could appreciate that you think the sort of straightforwardness and transparency was the answer there. And that brings me really on the topic of culture. And I know that at Boomi, culture was important to you. And I know it's been important for you as an intentional mandate to create a great culture at Guru. So I would love to ask you, when did you first realize how important culture was and what has it resulted in specific actions you've taken at Guru?

Totally. Yes. So many of our values now at Guru have some of these origin stories. You know what one, one I was just talking about, we, we call it seek and share knowledge now at Guru. But it's, it's, it's all about transparency. It's all about the relationship between transparency and trust. And that, um, I just have, have ever since then just been convinced that it's better to, um, share, uh, bad news, uh, or, you know, be direct, you know, whatever the unpleasant topic might be, you know, share it. Take people on that roller coaster ride with you. Assume people are smart and thoughtful. Assume people people will not, um, do, uh, inappropriate things with that transparent information you're sharing with them, right? And, and there's trade-offs in that, right? But, but I think, I think that's, that shaped one of our values. To answer your specific question about first realized, and I don't know that I would have called it culture or values then, but one of our, um, for our first angel investor at Boomi, um, whose name is Mike West, who's often referred to as the godfather of Boomi and was a key person and sorting through a lot of what I was talking to you about in those early days. He, he would always have this saying whenever we would interview someone for a role at Boomi, and what he would always say is, just make sure they don't take themselves too seriously. And you probably— I think I might have even used that phrase earlier in our conversation. And, um, I, I didn't really get it after a while, but I think the first thing he did that I've, I've learned is the the value of repetition and the need to say it over and over again. He would always say, he'd say to everyone who was interviewing, so just make sure they don't take themselves too seriously. And later, that's now become one of, and the first company value we always talk about at Guru. But that was my first clue. And what I later realized and what I really think he was getting at was the stuff we were saying before, right? The dangers of people who walk in with high ego. And with high ego often comes an unwillingness to be comfortable saying you were wrong, be comfortable being vulnerable, a debate style where you want to be right versus debating because you want to get to the right answer, right? All these things that are just toxic behaviors, in my opinion, to a high-performing team. And that— so that was my first introduction. I think at Boomi, I describe our culture as accidentally good. And that I think that we were thoughtful about that. I don't think we sat down and did nearly the energy we do today at Guru. But if I look at the humans that are still there, the ones, the ones I know, Boomi's a lot bigger nowadays, but the ones are still there, you know, really just, I think, embody a lot of that, you know, that first point, right, that don't take themselves too seriously. So, so that was sort of the first taste that was back in the early 2000s, in the early days of Boomi. And it's really stuck with me, I think, moving forward. I think at Guru, we first wrote down our values Uh, it was in 2017. It was when we had closed our Series A and we knew we were going to be hiring at a good clip and we knew that we were going to be opening a second office. And therefore, you know, the need to actually document and define your culture through a set of company values was critical to make sure that as that scale was starting to happen, we could start introducing rituals to both define the values and then reinforce them. And I think we've just sort of kept that rolling ever since.

Mm-hmm. I love especially that you realized it was because you were hiring and also because you were gonna be in two offices. So the notion of, you know, people who are geographically dispersed can't just run into each other. And so there has to be sort of connective tissue inside of your culture and to your point, your rituals. And I'm curious, how did that inform, how did that How does that inform your hiring? What— how do you specifically test for the right cultural fit when you're hiring?

Totally. Yes. Yes. That's, that's one of the first rituals. We use scorecards in all of our hiring processes. Our talent team has done a really thoughtful job in this. Every, every interview we do has a culture interview component, and that culture interview is done by someone who is not on the team., that the person would be reporting into. And, the purpose of the culture interview is to effectively reverse our company values into questions to test for behaviors that we value and think are important. And you've heard me use some of the phrases already, but, you know, one that I love that they use is around shared success. And so when, when one of the questions you'll hear someone ask is they'll want to understand accomplishments that you're proud of. And one of the things they're listening for is, does the person make it all about themselves, or does the person recognize that anything happening in a team environment is happening because of the team, right? It's, it's a team effort. And, and, and they're— what they're listening for specifically is, does, does that credit get given, right? And that, that as a, you know, real tactical example, I think, I think to your question, like That's a question that I think is just super telling around testing for that, that fit. In that case, it connects back to the don't take yourself too seriously, right? I think the people that, that tend to want to proactively talk about, you know, of course, I think clarifying the role you played in some outcome or something you're proud of, that's important. But also talking about the shared success and, and who was an important part of making it, making it work. Was great, you know. Yeah, a second one we do is really focused on vulnerability, which I think is also something that is, is, is, um, not necessarily something that might come natural. Or maybe a more empathetic way to say it is, in many cultures, vulnerability is not rewarded. And so people have had to grow up in a place where vulnerability is viewed as weakness, which I think is, is completely backwards. And so what we look for there is to try to see how comfortable candidates are in sharing things they did wrong or mistakes they made and what they think they learned from that. I think that we've just really made part of the process that has been a huge help as we've been growing the team.

Yeah, I love that about vulnerability. I love the expression, "The confident can afford to be vulnerable." I love that too.

Yeah, it's beautiful. Yeah, well said. Yeah.

And specifically, the notion of humility, especially the way that you talk about it, has to do with being a learner. And being someone who can pick up things and own mistakes and therefore learn from them. So I can imagine that has a great impact on business results. But I guess I'm wondering, are there any downsides to your culture? Do you see— when you talked about trade-offs earlier, do you see any downsides to having such a tight— either a tight cohesive culture or specifically your cultural values?

Yes, specific. Yes, maybe it's the same answer. I mean, you know, you use the word tight, and I think that was a good word because The more crisp you make them, you are intentionally creating trade-offs. And I think, I don't know that it maybe isn't even downsides, but I'll share a specific Guru one, but it can be downsides because there can be unintentional interpretations of company values. For example, I think in our case, I mean, when you really look and stack up our values and, you know, despite this, I wouldn't change them for the world, but, you know, we talked about people not taking themselves too seriously and vulnerability and trying to emphasize learning over blame or other behaviors. We also have one called Give First, which is like really making it clear that we value team members who give first, however you do it. Right. But, but the point is you're giving without expecting anything in return is the point of it. And it could be internally amongst your coworkers and you'll talk to new hires at Guru and they'll all talk about how welcoming and friendly and helpful their, their colleagues were. People who they don't even know yet are reaching out. How's everything going? You know, Or, um, or it could be, uh, giving to your community. You know, we, we think a lot that it's really important that, you know, uh, as a company is growing, you, you, you improve the community around you. You don't sort of extract from it and then give back later. You know, it's, it's how do you actually make things better along the way. And, um, and so, you know, you sort of have all of these, uh, I think behavioral guidelines and, and values that we think are important. And, you know, sometimes you'll hear people say, um, uh, there's a cheer culture at Guru, and I'll sort of go, what does that mean? And it'll— I think what they're getting at is sometimes there can be this feeling or sense of obligation towards positivity. And, you know, that's something that we've struggle with. Now, look, I'll take that any day of the week over the alternative, right? Which is like, I work with a bunch of assholes. Like, I'd much rather have that going on, right? But I think it has prompted us. Yeah, exactly. It has prompted us to go like, you know, okay, how do we, you know, how do we— I love the radical candor framework. I'm sure you've seen it, right? Obnoxious aggression, radical candor, rowanis empathy. How do we make— how do we put ourselves in that upper right quadrant? Right. We— I think we're not a company that's likely to fall into the obnoxious aggression side. So how do we recognize the need to balance candor with our kindness? Right. So it's prompted us to— and we revise, upgrade, revise our company values every 18 months or so. We're probably on version 3 now or working on version 3 right now. And we revise them as we learn this stuff. And so I think that was a good example where we were like, okay, let's just, you know, let's be aware of this first. Let's not ruin it because there's a lot of goodness in people cheering each other on and advocating for each other. And that's actually really good and positive and healthy. But let's just make sure we're balancing that with like, hey, you know, it's also really valuable when you give your team member candid feedback that might not be good feedback or positive feedback. But as long as you're delivering it with care, then, you know, that's phenomenal. We all want feedback, right? So that's, that's a good one. I think that we've, we've sort of like iterated our way through as we've lived that and seen the consequence of that. Again, I don't— I think it's a very— I think it's something we're sort of already moving on the other side of. But it's— I think it's a good example of your question of where you can find downsides.

Yeah. And I love your point about the Radical Candor framework because what I think people do is they use that as an excuse to be a jerk, right? Well, I have to tell them, right? But actually, to your point, it's so much more sophisticated. It's about caring enough, right, to then share with other people kind of what I see and then how can we work out that problem? Because conflict and also just being annoyed is like a normal part of working with other people. And so then how do we work that out together as a community? I think that's a powerful culture.

Totally, totally agree. I think it's so well said. Yes, I totally agree with you on how it can be weaponized. And I think the whole point is, and maybe the word radical isn't the best word, whatever, to your point, it's really all about like, you have to show up when that hard conversation and you actually have to care about the person. You have to authentically care about them improving, getting better, being successful, whatever it might be. And as long as that's— as long as that's the underpinning of what you're then saying, great. Right. I think— I think where people will quickly lose trust or things will go from bad to much, much worse is— yeah, I think that squarely moves you into the obnoxious aggression and you're— you're— you're— yeah, that's— that's— that's worst of all. Worst case scenario for me.

Right, right. Where you don't want to be. So you talked about doing this when you sort of started this, when you were going to have two different office and then, uh, pandemic. And so from pandemic, I'm assuming you, like everybody else, started working from home, and you may have actually a diffused workforce.

Yes.

Um, how have you maintained your culture and kept everyone in sync kind of during the pandemic? And what state are you at now in terms of remote work, hybrid work, in-the-office work?

Yeah, um, to your first question, we, I think, have an immensely thoughtful and effective people team that really puts the, the company culture and values at the center of so much of what they do. I would say one good thing is because we sort of connected our company values work with our second office, it was an example of us going, not everyone's in the same room, and that's going to be our reality. You know, from the early days, we— and I did the same thing at Boomi, you know, we believed that the two-office strategy was, at the time, was a great way to ensure that we're diversifying the skill sets and backgrounds and experiences of the different roles we're looking to fill at the company. And so that, that I think defined a bunch of habits and rituals around how we actually bring the values to life that do not have any in-person expectation or assumption, whether it's, you know, in our town halls where we do— we call it values in action. And basically values in action is, is guru employees nominating and, and basically showcasing their colleagues who they see living a value and what was the specific thing and why. And so in our town halls, we walk through— here was the value, here was the thing— we thank the person, we talk about why it's connected to a company value, you know. So that kind of thing I think scales really well and does not have any location dependency. I think another one that we do that I think people value and love is, um, uh, I, I meet with, um, each month's kind of like cohort of new employees that are at the company and walk through the values and talk about why they exist and what they mean and, and ask for candid feedback. So what resonated, also what was confusing, um, and, and what, you know, where do you think we might be able to improve them? And I— it's one of my favorite meetings we do and, and the new, the new team members are super engaged in it and they love it. And so, so I think those things, I think those are some examples of rituals we've done that, that are sort of like location agnostic. And I think will hopefully set us up for just, I think, and there's so many more, right? But like all these rituals, I think just, you know, the more you put into them, the more you will be able to look at a company when it's 500, 1,000 employees and go, Hey, this really scaled with us. And so much of the rituals we do actually came from team members. You know, we didn't come up— the two examples I gave you came from people who saw them happening at other companies and were like, this is cool. I was like, awesome, cool, we're going to do this. And then we started, you know, we started doing it. And so, you know, what kind of happens is when, when you really make it clear you care about your culture and your values and then you hire people under that premise, they care too. And oftentimes it's a really important reason of why they chose to come and join your company. And so it snowballs, you know, they bring ideas with them and you can kind of really create this, this cool thing. Um, and so, so yeah, and then the, the sort of logistical part of your question, we're, we're hybrid. Um, we have, we have our offices in Philly and SF, they are open. Um, and we are hybrid, uh, and we are also, um, fully remote. So, so we effectively just gave every employee a choice of what they wanted to do. The only ask was that they share that intent with us, and, and they can change their mind later. But really, for office planning purposes, we really need to have a sense of what are we doing. And again, our team's done an awesome job with our workplace strategy. And just, you know, we do hot desking, which really allows our, our floor plans to scale as we continue to grow. Of course, we have our desks much more more spread out these days than we did before. Um, and so, so I think that, that sort of proactivity has been great. But I think we, we just sort of went into this thinking like, hey, we're not going to, you know, we're not going to impose some sort of mandatory, um, attendance policy, you know, really just, really just, in my opinion, honestly, like, there's lots of things that are hard in a remote work context, but I actually think there's also just as many advantages. And so, so I tend to look at it like that and say, well, let's, let's actually like leverage the things that are actually better. When you can have this mix of at home, in your office, flow state, uninterrupted work in an office, creative meetings, strategy planning meetings— yeah, you want to be doing those in person, right? If you can, you can actually do a best of both worlds thing that I think is Like I said, I think it's actually an advantage. I don't, I don't view it as a, as a challenge so much as an opportunity, um, that I think is, is, is like, is a net positive for Guru.

Yeah. Yeah. I could see that. And then I think it's about allowing the creativity inside of that canvas, right? Of all these different possibilities and probably people learning together what combination works best for them and for their team.

Yes. Yes. Cause who knows? Yeah. We don't know yet. You know, our office has only been open for a month. And so to your point, that's right. You know, people inevitably change their minds. I've talked to people who are like, boy, I forgot how terrible a commute is. Yeah, you know, they've really dialed back their in-person things. Or like our creative brand team, so much of what they do is, is, is creative work, brainstorming ideas. They want to do that in person, but they just have a schedule that they use when they know they'll all be there to do that work. And then the rest of the time they're home, you know. And so, so yeah, to your point, it's like I don't think it's the same for every team, and I don't think it'll be the same period. I think it'll— like, people will just learn and evolve their thinking as they go.

Yeah. Rick, you speak so confidently as a leader, and I just have to assume you weren't necessarily born with that, you know, and sort of your own style as a leader. I guess I'm curious, how have you grown as a leader, both in terms of from your first to your second company, and then also as Guru has grown? What would you say the changes and growth spurts you've done as a leader?

Uh, well, thank you for the compliment, first of all. Um, I, uh, I have definitely not always been confident. Um, but I think, um, yeah, maybe a couple thoughts on, on, on sort of personally. I think there are skills that I maybe better understand as I've grown up because, you know, as you said, I've really just started two companies. Like, I was only working at another company for two years and then started Boomi and then started Guru. So, as a result of that and over that period of time, I think some examples of things that I think are important now, the first would be like empowerment. And I think I didn't understand the value of being intentional about empowerment and how empowerment is actually really tied and connected to recruiting and the type of people you really want to bring into your company. I think I learned probably the hard way that, um, I, I, I describe it as like when you start building out your leadership team, you shift from showing up with answers to showing up with questions. And I think that that's like a, an example of what I mean by that, of, you know, with intentional empowerment, you know, the leaders that you'll bring will actually expect that and thrive on that. They want that. They want to have permission for, and they crave autonomy. And by the way, they also value doing that across their teams as well, which is, which is, you know, sort of even more important because then it scales. So I think that's one good one. I think curiosity is one that I've learned. I think I've always been curious in the sense of like learning from a product perspective or markets we're going after. But I think what I'm really getting at is sometimes I can feel impatient about something that isn't maybe as happening as fast as it would. Or if something didn't go quote unquote well, um, what, you know, let's really sort of understand that and start dealing out blame. And, and I think instead of that, what I think is actually much more effective, um, is showing up with curiosity and asking questions and not showing up with assumptions. And, you know, there's a balance there with being decisive, certainly, um, depending on what it is. But I think what I'm really trying to get at here is like I think being curious leads to, you know, it gets you away from right and wrong and it gets you towards learning and growing. It gets you towards going, okay, this thing didn't achieve what we thought it might. And we learned these 3 really important things and we're now going to use that for the next thing. And that mindset versus everyone doling out, you know, the slice of the blame pie and pointing fingers at each other, which really doesn't do anything to make your team or your company any, you know, any better.

Yes, but it does make everyone mad at each other.

But it does make everyone mad at each other. Yeah, exactly.

Um, yeah.

And then maybe a third one I would share is like, uh, uh, um, leading with empathy, which, um, again, like, recognizing the importance of it more so. So like, an example of this would be like, I, I force everyone who, who works for me to vent about things. And it's venting and we don't have to do anything about it and we don't have to, you know, solve it. But let's get it out, right? Let you know. And I think that relationship and like that can be some of the best ways to spend a one-on-one with someone on your team is, is giving space for that, but welcoming it really. Welcoming that kind of dialogue to happen. And then I think I've struggled with this, but I think what I've learned, I said, and don't solve it. What I really mean by that is I think I try now to go, well, what can I do to just ask the question? Do you need help solving this? Is there a different conversation we want to have? What can I do to make sure you're feeling supported? That was in a lot of ways for me a big pressure release valve because when I started asking that question, well, people would just tell me sometimes they actually did want help with the thing. Sometimes they just wanted to complain because they were having a bad day. Right. And I think rather than me guessing, which I think I would do in the past, I think now if we just have that conversation openly and then I go, hey, what What can I do to make sure you're feeling supported here and that we're, you know, they'll tell you and then, and then act on that and move on. So I think that was something I've really valued kind of learning over the years.

Yes, I love especially all the coaching questions you've kind of like worked your way into because to your point, like people want to go off and do their thing. And I think founders have this incredibly intense feeling of accountability and I've got to solve it.

Yes.

And then when you put back to your point about empowerment, when you kind of give it over to the employee, like, I hear you, I hear you, and that kind of sucks, and how can I be helpful? It both puts agency over there, over to them, and also it helps you really understand what are the keys here to this situation.

Yes, yes, yes, absolutely. I think the agency point you're making, totally, totally agree. It's like, look, I will, I will help you as much as you want me to help you, which might be not at all. Or it might be a good bit. It might be a situation with a peer where I have to be involved to some extent.

Right.

Yeah, I totally agree. Yeah.

So Rick, with all of these experiences, have you ever experienced self-doubt or imposter syndrome? And if so, how did you handle it?

Oh, yeah.

Both. Tell us about that.

Quite often. The imposter syndrome one is a really interesting one. You know, that one I remember very vividly in the early days of Boomi, starting a software company in Philadelphia where there really weren't any. And, you know, this was the 2000s, and so Silicon Valley— not San Francisco even yet, you know— but Silicon Valley was very much the center of all of that stuff. And as we started, um, improving our market and growing— excuse me, improving our product and growing and, and kind of figuring out our market, we started to understand who our competitors were. And I remember thinking like, oh man, like they've raised, you know, you know, 10 times as much venture capital as we have. And, you know, they're, they're building products in the epicenter of where all the greatest stuff happens. And, you know, all of these kinds of feelings of, of it's, it's, it's a, it's a founder kind of maybe a special kind of founder imposter syndrome. I don't know. But it was in my case, it was very much like, Oh geez, like we can't— can we actually, you know, go toe to toe with these kind of companies? Like, can we even be in the same room or whatever? Well, we started winning deals and then that really changed everything. And then, and then I was like, oh wait, like, yeah, they're using the same programming language as we are. And if this person over here has this skill set and this person on my team doesn't, but, but this person on my team has grit and is just going to figure it out, like, no, I'd probably rather have that anyway. Right. And then, you know, on the venture capital thing, it shifted to like, oh, right. So I actually, you know, a dollar, a dollar raised for at the time, right, a Philly-based startup company is quite literally, you know, 5x, get you 5x as far as a dollar raised in the area when you look at cost of living and all kinds of expense, everything. So, so I think that kind of faded away and it took— I think it took some some, you know, uh, like, see, like, actually just sort of like getting into it, getting into the, the, the, um, the market and seeing who the competitors were in the dynamic. Um, the self-doubt one, uh, that one never really ends, at least for me. Um, and I think self-doubt for me will manifest in, you know, big strategic questions that I'm trying to answer about Guru, or, uh, you know, the entirety of the pandemic as a specific example of what to do when there's literally no playbook and there's no, you know, there's no like, oh, here's best practice, right? Um, and so, and so what to try. And I think, I think how I've gotten, how I've gotten better about self-doubt is, I think, a few things. Like, first, um, I think there's a decision-making framework that's nothing new or inventive, but it's the idea of reversible and irreversible decisions. And when you start thinking that way and you recognize that the vast majority of decisions you make are actually quite reversible, it's very freeing. It connects back to what we were saying earlier about it also— it also gets away from right and wrong and just gets you into the idea of going Okay, the only real mistake I can make is not making any decision. But as long as I make one, because there's few topics, but most topics are very reversible decisions, as long as I make one and I make it quickly, we're good, right? Like, like, we're going to learn stuff no matter kind of what happens. And so, so that's gotten past self-doubt, I think, for sure. I think mentorship is also something I've always valued and continue to value. I like— it's, you know, for me, it's like What, what can— what, you know, who do I know that I can reach out to that is a stage or two further along than where I am at in my role? And how can I just sort of have them maybe not on speed dial, but sort of have enough of those folks that are sort of like, like where I feel close enough with where, where I can ask them the question in a very candid way and just sort of get their advice and do some pattern matching on what, what I hear after I ask the same person kind of 2 or 3, 2 or 3 times. And I think those things, um, have been a big, a big, a big help. And, and, you know, there's an anxiety that can come with self-doubt. And I think the other things, like, if I was going to share something with a, a younger version of myself or a founder or whatever, it would be something like every, like, work thing that I stressed out over and got really worked up over and got myself all, you know, you know, anxiety'd up over really just wasn't that big of a deal. When I look back, it's very, very rarely as, as bad as it feels like in the moment. And I just sort of link that to self-doubt because I think you can just sort of disarm it a little bit by going, you know, hey, remember those last 3 or 4 things? This will probably be like that where you'll look back in a month or two and go, oh yeah, anyway, I'm not sure what I was so worked up over.

Yes. I love that. Everyone should know that. You know, I guess my last question on the topic of advice for your younger self. What do you wish you had known? What else do you wish you had known earlier on your journey?

Yeah, totally. Let's see. Some of these may be themes I hit on, but here's one. Here's one I didn't. Here's, here's one I didn't talk about before and is definitely the way you frame the question, something I wish I had known. I think I have definitely in the boomy days and will still catch myself doing it with Guru, overattach myself and my maybe identity or sense of happiness or satisfaction to the company. And I think that's a huge mistake. And I think it's— nothing good can come from that. And I think there's, you know, every startup journey is not the straight line that it might sound like on a blog post. It's always the squiggly lines, and it can really, really drag you down. And I think having that— I wouldn't say I know how to do it, meaning like how to separate yourself from your company. I think maybe just over time I've gotten a little better at it. I think I've gotten gotten better at prioritizing interests that have nothing to do with work, like family and friends and hobbies like music and things like that, and making that more of a priority than I did with Boomi. But, um, I think that that identity thing is very real. I think it's been real for me. I still find myself feeling that way at times. And I think, I think the more that any founder can recognize that that is not the reality, uh, at all. And don't get caught up in the hype of the funding round of whatever's going on at this company, or the award happening over at this company, or the, or the, or the— is wasted energy, honestly. And, um, and it's not productive and, and damaging. Um, so I think that would, that would probably be near the top of my list.

Yeah, wise advice. And, and What great wisdom, Rick. I just have to say, it was such a pleasure to meet you and such a joy to hear your thoughts from your journey. And I just want you to know that everybody's going to find this very, very valuable. So thank you so much for spending the time with me and for sharing all your wisdom.

Well, thank you. It was a really great conversation. I very much enjoyed it as well. Thanks, Alisa.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.