#36: Hubert Palan, Founder and CEO of Productboard — the challenges of scaling leadership, tactic...

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.

Welcome, and I'm thrilled to have Hubert Pallant on the show today. Hubert is the founder and CEO of Productboard. Productboard helps product teams understand what customers need, prioritize what to build next, and align everyone around the roadmap. Productboard is used by over 5,000 customers, including Microsoft, Zoom, and Volkswagen. Hubert and I connected at Web Summit in Lisbon in November 2022, and you can hear the background noise and the hubbub of Web Summit in the background. It was fantastic to sit down together for this podcast. He's raised over $260 million and Productboard is officially a unicorn. We had an incredible conversation and we talked about the big challenges of scaling leadership and specifically the markers that show that an executive will not be able to scale and the kinds of conversations you need to have with them when you see that. We talked about how Hubert raised so much money, his specific tactics for fundraising, and how he flipped the script and did diligence on his investors. As they did diligence on him. Hubert also talks about his mood meter and why he built it and how he uses it. And we talked about how Hubert balances his time as a founder, a CEO, a husband, and a father of 2 kids. It's an incredible conversation. You're gonna get so much out of it. So please enjoy my incredible conversation with Hubert Pallant.

Hubert, welcome to the show. I'm so excited to be podcasting with you. Here at Web Summit here in Portugal, and I'm just excited to have you. So thanks for coming today.

It's so great to be here.

It's, it's a pleasure to have you. And we connected because we are doing a panel together at Web Summit because you're also a UX/UI design expert. So why don't you kind of lay the stage? Tell us a little bit about your background and tell us about your company.

Yeah, I, um, Hubert Paulan, the founder and CEO of Productboard. It's a product management platform. Think of it as Jira or Salesforce, but specifically designed for the needs of product organizations and product managers. As it turns out, there is a lot of project management systems that help people break tasks into small tasks and get them done. But product management is not project management. Product management is about customers, their pain points, and what is it that you should ultimately build for them. And there's really no systems that help you get that understanding. And we said, like, let's build a platform that will centralize all the customer data, that will help you understand how the different customers, like the different customer segments differ, who needs what. And then hopefully, ultimately, you're going to get that translated into a product roadmap that is going to be helping you, you know, against your product strategy and achieve your product vision, but in a very thoughtful, systematic way.

Got it. And it's a tool for product managers.

It's still for product managers. The thing about product, like we have customers like Zoom or, you know, Volkswagen, like small and large companies. But the thing about product management is that there's product managers that are making product decisions, but everybody else from the company needs to understand the roadmap. Everybody else wants to provide input and have ideas and salespeople talk to customers. Right. And so it's a very collaborative process.

Ah, that's right. So it helps everybody give that input so that ultimately product managers know what to do and to build.

Like at Zoom, we have like 1,800 contributors from across the company, like because people need to have visibility and be part of it, right? Let's say you're building the product and it's, you want that alignment and the sense of belonging almost.

That is so true. I'm going to start with empathy because empathy is one of your most defining characteristics, as I sort of just saw. How do you define empathy?

It's ability to feel how others feel. That's how I define it. So it's not, it's like your ability to put yourself into other people's shoes and understand like in a situation how they would feel, you know, respond to a specific external input. And so, you know, it's not necessarily, It's not the positive aspect. It's like you can have empathy for negative— you can treat people with empathy in negative situations. And the reason why I'm saying it is because we actually have empathy as one of our core company values because it's so important as a product person to empathize with the customers, and it's so important as a leader at the company to have empathy with your coworkers, employees, colleagues.

Right.

And so, yeah, I just think it's a very defining characteristic both for product and leadership.

Yeah, I was going to ask you about that next because I hear— I understand and agree that you need to have empathy to be an effective leader. But can you make the case to people who think empathy is a nice to have? It's about being nice. By the way, empathy is not about being nice. So tell, tell me how come it helps you as a leader specifically scale a company.

Well, you know, there's times that there's the great times and there's tough times. There's always things that are not gonna work out the way you want it. And as a leader, you need to effectively address and lead in both times, right? So like when the times are great, like you're talking about the mission, it's like, look how great we're doing, look at the impact and so on. But equally so when times are tough, you're gonna be saying like, unfortunately this is not working out. Like we screwed up something or, you know, macro right now, right? Recession pretty much. And you need to address it in a way where you understand how it makes people feel, even if it's negative news. You lose a customer and you need to translate it to people, or you give somebody feedback that's, you know, constructive negative, and you need to absolutely do that. Like, if as a leader you want to help others to grow, you do that by giving them feedback that's negative. Of course, like, you know, you reinforce positive behavior and all that. But so that's where the empathy comes into place because if you do it in a way that's insensitive, that doesn't understand like the people's emotional reaction and, you know, the shock sometimes, like there's, you know, I mean, who goes around and gives negative feedback to others around them in the world, right? Like, so especially like people who are entering careers, you know, early on in their careers, It's something that you need to develop.

It's so true. I think that's really well said. Actually, in my book, From Startup to Grownup, I say at the very opening line, leadership is an unnatural act. And actually, the act of giving feedback to people is an unnatural act. And so then you have to develop it. I'm just curious, how did you personally develop your skill of giving feedback to people, especially when it was a difficult message you had to have?

Yeah, it's— You know, it's a journey, as you said, like you're not— people want to be liked naturally. And you know, it's slightly different, like in a family when you have very closely built relationships and you have very deep sense of trust, like you don't shy away. Like people argue with their parents, right? Like they're very critical, but it's a very different thing to do with somebody that you don't know that well, which is why, by the way, the whole idea and concept of trust is so important and having close relationships with people because like then you can have these candid conversations and you can be more direct in a way that feels more natural. Like, you know, you can be much more direct with your close friends, with somebody. So anyway, so the thing though, it's as a startup founder, you know, you have so many situations and opportunities to learn that because inevitably if you are, you are optimizing for the success of the company and you are critically evaluating the progress, right? And you have the most context because by definition you've been there the longest. Doesn't mean that you are smarter, that you're like, you know, that it's— that's not what it's about. It's, it's about the depth of the context and understanding of the market and where you operate. And that gives you the unique perspective to give feedback to people like, hey, it could be better. I talked to all these other founders, I talked to other, you know, CEOs or leaders in similar situations. So you, you know, ideally you're very thoughtful and methodical You should surround yourself with mentors and so on. But the reality is that a lot of people are just basically thrown into the water and swim. And the important thing is to understand that you shouldn't avoid it. And the fact that it doesn't feel good doesn't mean that you shouldn't do it. If anything, if you have that intuition like, oh, I don't want to do it, it almost the signal that you should do it. You know, because it's like, you know, rationally, like, hey, that needs to be done. I just, I just Avoiding it, which is like, go do it, even if it's a difficult conversation.

Yeah, I think that's very, it's very wise. Many, maybe almost all of the startup founders that I work with at some point are avoiding having a difficult conversation. And I think what's worse, and I want to get your take on this, what's worse is when their, I'm sorry to say, misguided HR person, or at times misguided other executive or misguided co-founder, is telling them, oh no, give them a chance, or whatever, or no, like, no, you can't do do that, even— and not about firing them, just about having a direct conversation with them, which is really about performance management. Have you ever experienced that? Like, you have an inclination yourself, like, I probably should have this conversation, but then you have someone around you saying, no, don't do it, it's inhumane. And how do you overcome that?

I, you know, inhumane. I, uh, again, I think that if you're acting with empathy and if you come from a place where you are acting in the best interest. I mean, obviously the company, but even in the conversation, right? Like you're trying hopefully to help people see that things can be better and you should do it in a sensitive way, but like you, you shouldn't avoid it. And so I would say, um, the situation that you're describing, it's more of an, it's very difficult to get outsider, outside person's perspective who doesn't have the depth of the context, right? So, like, you're going out and you're talking to, you mentioned HR, people teams, and they can give you an answer only on, like, a surface level, right? Like, best practices, and there's obviously, you know, learnings and there's science, human psychology, right? And how to act. But at the end of the day, you need to make the call because you have the context. And, you know, the other thing is you need to move fast. And so, and then again, this might be unnatural and kind of, you know, unfortunate, but business is the number one responsibility of the leaders. And so you need to do whatever is best for the business, even though it's sometimes difficult on the individual level, which by the way is super hard as a founder leader, 'cause you find yourself as the company grows, frequently in these conversations where the needs of the business are kind of outgrowing the abilities of the individuals.

Yeah, I know it's hard. For those of you listeners who aren't watching this, Hubert is making a face. Is it very difficult?

It is.

And actually, I'm going to make you another more difficult question. As we were walking over here, we were talking about what founders often ask you. So Would you share, because when you do roundtables or fireside chats with some of your VCs, what is one of the common questions that founders ask you about sort of the executive team?

Yeah, it's a lot of, you know, I joke it's almost like founder support groups or like, you know, whenever it's very interesting because you as a, especially like I'm in a CEO and founder position, position, right? Like not everybody's a CEO founder. But in that role, it's, you open up very quickly to others because there's very few people in the same role. And so you somehow surprisingly get like very deep in a very short period of time. I just had a meeting with the CEO of ClickUp and like we immediately started talking about the challenges of leadership and scaling companies and so on.

Yeah.

But anyway, to your question, a lot of it is about building teams and scaling the leadership of the companies, especially if your company is growing fast. It's kind of a constant team building exercise. And it's like, do you have the right players? And, you know, I mentioned it's a little bit like building a sports team. The difference though is it's not like you build a sports team and you go to the Olympics and you gel the team and you have like the whole tournament to win together as a unit. The challenge within the business is that you constantly keep building the team and replacing players, right? Because like the needs evolve, especially if you're a fast-growing company. And so that is the very difficult leadership, you know, dissonance, like the conflict is that on one hand you're trying to build a very tight team based on trust and gel and kind of like the unit almost, and on the other, you are constantly replacing and building and upleveling because the needs of the business evolve. And it's a conundrum that a lot of the founder CEOs talk about and like, how do you balance that? And, you know, like how, how, and I, you know, yeah, anyway, I'll stop. I'll stop.

Well, I was gonna say, how have you balanced that?

I know.

That's a, how do you have the magic answer?

Yeah.

I, you know, I feel like that. If you have senior enough people at the table, you can have the conversation early on saying like, hey, there's a phase of growth that we're headed into. This is what we need in terms of the leadership skill, the depth, breadth of the role, but it will evolve. Like, if we succeed, ironically, um, that will actually create more change and the need to broaden the role or break it into multiple, like you won't be able to lead that entire piece of the company, right? Suddenly you will, we will need to have multiple leaders and that will decrease your scope, right? Or, hey, we will need to bring on board somebody when we reach a certain revenue milestone, headcount milestone, like whatever milestone who's seen the scale and you haven't seen it, right? And there's obviously always exceptions. Some people have scaled from companies like super small all the way But it's very rare.

Yeah.

Like in the grand scheme of things, you know, people typically tend to be specialized and they tend to be really good at certain phases of the company. And so, yeah, so that's my answer. Like to the extent you can kind of have that conversation upfront so that it's not surprise and so on. And it's not like we're not getting into a marriage. It is much more, you know, I mean, hopefully people enter marriages with like the, I want it to last. And not like, hey, this is just for the next 3 years and then we'll see it.

Yeah.

So that, yeah, I, you know, late and I've seen that later on. Like again, I said like, and it requires a certain level of self-awareness and maturity of on everyone's part, right? Who's on the team to have that kind of conversation.

Right.

Is there a signal that you get because it's, you, what you just said was like, oh, for 3 years or for a milestone. And that's kind of like on average, is there something that happens or can you give an example of a moment where one of your senior team, you saw this is a great player, but it's not gonna take us to the next level. Like, is there a marker or a signal that you saw?

Um, I mean, you know, the situations differ so much. Like sometimes when people become overwhelmed, but it's like that sense of like, oh, there's so much, there's, that is a signal. You know, like, oh, okay, because that means that you, like, psychologically, you are not, you know, you're not, you're not succeeding with under— like, pulling your, uh, pulling yourself above it all. Like, okay, it's complex, but I'm gonna tackle it one by one. It's kind of like, you know, the ability to see beyond where you're at. And it's like, if you're overwhelmed now, it's only gonna get worse if you're— again, This is all assuming that the company is growing, right? It's very different if you're like a stable team that's not growing.

Yeah.

But it's not what typical startups are about, right? Um, so, so, so that's one. And then just like, yeah, in the conversations, like, how are you— if you talk to people about how do you see the organization evolve and how do you see your role evolve, and then you can, you can get a sense for like, you know, are, are they aware?

Yeah.

Do you do— are they bringing it up themselves. Like, hey, this is what I'm good at. This is where I know I have gaps. And, you know, I might need help in certain areas. So that kind of conversation reveals a lot about how people think about the evolution.

Yes, that is very well said. And I think what— so I just also want to summarize for myself and for the listeners, like, what often happens is an executive or, you know, just a leader will be overwhelmed. And they'll tell you how overwhelmed they are. And you, the CEO, might be like, "Oh, I'm so sorry you're overwhelmed. What should I do?" Actually, that's right there, like a sense, "Huh, maybe it's the person not fit for role." And they can be a wonderful person but not fit for role. And also, to your point, are they showcasing in the conversations an awareness of where they are and where they're going? That is such a powerful answer. Thank you. And it requires you, the founder CEO, to have the wherewithal even if it's your first startup, to be like, huh, I think there's supposed to be a different way. How do you shift your identity, you know, 6 months, 6 months, 6 months at a time to make sure you're at the level of recognizing, oh, I'm supposed to be evaluating if this is going well or not?

Yeah, it's interesting. It's, you know, to some extent, founder CEO, I feel like is a specific role from other founder roles in the sense that the, like, the founder CEO is really the role of a coach and making sure that you have this strong team around you, which, you know, on one hand is incredibly hard because like, you know, you need to be able to evaluate all the other players and teammates. On the other hand, it gives you a little bit of a break and I'll explain, right? It's like, If you are a founder, you know, CTO, if you're a founder, CMO, if you're a founder, like whatever other title, like you have to be in the department-specific role. You need to be the deep expert in that domain. And you can't like rely on mentors and coaches and, you know, people that will help you in that role. As in the CEO, you can more, you know, it's like, hey, what would you do? Like, You know, your, your role is to find the best people to run the different parts of the business. You understand what I'm trying to say? So you're a little bit insulated almost.

Yeah, it's a great point. You don't have one, you don't have a single department that you're responsible for. You're responsible for conducting everything.

Exactly.

So it gives you an advantage.

It gives you an advantage. But you know, obviously the difficulty is like you are still in the role where you need to evaluate whether you have the right people in the seats, which is very difficult if you don't have the deep domain-specific knowledge.

Right.

Right.

But that's why, like, if you see, you know, what great investors and great VCs do, they constantly expose the CEO to the best people in that domain, like in the world.

Yeah, right.

Like, hey, Hubert, you should go to this CRO at this company that I think is like world class. That happens all the time, right? Like, and in all the, all the different aspects. So So it's interesting from the founder's perspective, like you're learning by being exposed to the best of the best. And again, like you are not necessarily expert, but if you have enough of these conversations, it's kind of like a pattern matching, right? It's like, hey, I just had literally 100 conversations, you know, over the years of this. Like I've been doing this for 8, 9 years. So yeah, with top leaders and in the specific domain. So it's a journey. Like you don't know at the beginning. You don't know.

Yeah. But I think what you're also saying is you have to, whether your VCs do it or you do it, you have to expose yourself to those world-class experts and also to the experts in the domain areas like, you know, the best CMOs, the best CTOs, but also to other CEOs who are probably a few stages ahead of you.

Yeah.

And then you have to— I think the job of the CEO founder is to learn rapidly.

Yeah, absolutely.

Yeah.

Yeah, that is— I mean, yeah, you have to be push yourself outside. If you're not like a natural extroverted person, like, you have to overcome that. There's no way around it. You need to push yourself to be exposed, um, you know, to other perspectives and opinions and learn from others as fast as you can.

Yes.

So, speaking of high growth, which is what you were talking about before, your product board is a unicorn, a fancy famous unicorn, over a $1 billion valuation. But it's not really about the valuation, about the fast growth and success of the company, and it's also not about the fundraising. However, I think you've raised $261 million. Is that right?

Yeah.

And by the way, you've been around since 2013. Is that right?

Yeah.

And you were founded on November 1st, according to Wikipedia. So happy anniversary. Happy anniversary.

I don't think it's accurate. Like, how do you define— like, is it the filing of the incorporation certificate in Delaware, or is it when you quit your previous job? Like, when is the Chilofauni. Yeah, many birthdays there, right?

Many birthdays, I agree. But meanwhile, you've raised a lot of money, let's agree. So I guess I'm curious, was fundraising natural for you? Was it something that was easy? And certainly, what strategies have you used to fundraise successfully?

Yeah, I'm, you know, we're on a D round now, so I, but every round is different, every stage of the company is different. Ultimately, You know, you're asking if it's easy. If your business is doing well, it's easy. Like, this is— the investors are looking, they want to make a good investment, they want to return, you know, they want to create returns for their investors, right? It's limited partners, general partners, all of that. It's— so it's the business fundamentals, right? Like, and of course, different stages. Like, early on, you need to have a very crisp vision and You're selling the dream and you need to be very specific and you need to be able to articulate not just the immediate thing that you're working on, but like, why is it gonna be a big thing year, 5 years, 10 years from now?

Yeah.

Like, you know, what's the opportunity? And so that requires you to think the long term, have that vision, but then at the same time, not confuse the vision with the immediate execution that you're gonna do. You know, you need to be able to say like, hey, I understand that this is This is what it could be, but I'm gonna approach it, you know, step by step. And then you're constantly selling. Like you need to be, you need to learn to articulate it in a way. Like if you're a, you know, sales, salesmanship is about empathy. It's the same thing. Like understand who the people are, what is it that they need? Like how do things that you're saying or acting, you know, how is it making them feel? And so fundraising is the same thing. Like, can you articulate it in a simple way? Simple way. Can you find people who understand the problem that you're solving and create a relationship? Early on, you know, I made a very typical mistake. You're just trying to raise money from everybody and you talk to every investor, right? And you have a list and so on. And it's such a waste of time to talk to people who don't understand the problem that you're after. Like, you know, when I pitched to Ilya Fushman, our now board member from Kleiner Perkins during Series A, he used to be head of product at Dropbox, like he understood the pain points of product managers so well. It was the easiest pitch. He was like, yeah, I get it. You know, in like 20 minutes. And then when I pitched to investors that were like finance backgrounds, it was like, it was like, oh wait, how does it, like, what is it? Is it roadmap and prioritization? Like, can you explain that to me? And it's just, you need to qualify out quickly and focus on the people who get it. And of course, like, if you can't find anyone, then you need to broaden the scope, you know, and like talk to others. But yeah, the focus is critical. I don't know, there's so many fundraising, there's so many points. I, you know, happy to elaborate.

Yeah, well, give us a few more because you talked about in Series A, you're really selling the vision and the dream that makes complete sense. And you also want to find people who are going to get it, right? So the finance people or even some of the tech people aren't going to understand what products what the pain point in product is, but the product people, they get it, right? Just like you got it. What about— I'm going to sort of skip ahead to like later stage, like Series C and Series D. What do investors need to see? And also, how do you think about your process to meet the right people and then ultimately to have the right conversations?

Yeah, you know, later stage financings are much more about the business fundamentals, you know, metrics, performance. Like, you know, do you understand unit economics? Do you understand when you add a dollar somewhere in the business, what is it going to yield on the other side, right? Like, what's going to be the impact?

Hopefully more than a dollar, just to clarify.

Yeah, that's the right answer. Exactly, exactly. Um, I mean, there's a bucket of investment. You're making bets, right? And, but, you know, again, ideally it's isolated. It's like, hey, we're making these strategic bets, or, you know, like, we're making bets and we don't know how it's going to work out, but it's like a certain of the budget, right? It's isolated. And so it's like, for the most part, obviously it should be more than valid. Um, so in that sense, it's almost like a little easier because, you know, if you have the fundamentals, you have the fundamentals. If you don't, it's difficult. And you need— then you need to find it, you know, it's a different story. Or like, you know, explain that maybe you want to pivot somewhere, you want to add a new line of business. And then you're almost again back to the Series A explanation, right? Like, hey, we're gonna die for Diversify, or, you know, hey, we want to acquire a company in this space because we see this big opportunity and this is what we're going to do. And then you're again selling the vision, right?

Yeah.

Um, but so that, that, that depends. And then there's a lot of conversation about the team. And I know that the team is always the case, like early on, like, do you have the team? But early on it's more like, do you have the grit on the team for, it's like, people who will push through the early difficult stages of finding correct market fit, right? And finding go-to-market fit. And so later on in the later stages, it's much more, do you have the right executives with the right level of experience? And again, to what we talked about earlier, it's never set in stone, but it's just like the investors are evaluating your ability as a leader. Like, do you see the weaknesses? And they would, they would call you out. And then, you know, in later stages they would go and they would interview the executive team.

Oh, wow.

How does that go?

Well, you know, it goes, it depends. I mean, you know, like you introduce them to people and then sometimes they come back and some people are very direct and say like, hey, what do you think about this particular department and the leader? And they're doing basically the same conversation. Like you just asked me about like as a CEO and your team, like trying to get understanding of how self-aware the CEO is about the gaps in the organization. Yeah. And so, and then obviously it's, it's again a balance because, you know, like how much do you reveal to an investor that you know about weaknesses in some part of the organization versus kind of, you know, showing strength and like kind of being confident that, oh, you're doing it all right. Right. So it's a balance.

Yeah.

But you know, again, like, you know, some of the best investors that I encountered, like they have this ability, like super high empathy They build relationships, right? The, you know, it takes time. I mean, historically it would take time, right? It's not like, hey, you show up with a term sheet in 2 hours after the first pitch, right? It's like, what's your ability to assess the company? So anyway, so it's, I've definitely seen that in the later stages, the good investors do evaluate the ability to execute, like the ability to scale, Again, different skill set early on.

Totally. That's really well said. Now, I think one thing that you do, Hubert, that I think everyone is supposed to do, but I know that you actually do it, is you do diligence on your investors. They want to come in and give you money? All right, well, prove you're worthy. Who taught you to do that? How do you approach that, the diligence on your VCs? Because it's all like, you know, sometimes the VCs are like, all right, you want our money? And then they don't want you to ask them a bunch of questions, right? They have a little bit of, how can I say, let's say moxie. So how do you approach that?

Yeah, well, you know, I mean, like, like with everything in life, probably like you wanna be surrounded by people that you can trust and that you kind of can understand how they're gonna act in variety of situations. And so, like I said earlier, there's good times and, you know, in good times everybody's all, you know, rainbows and unicorns and lovey-dovey and all all that.

It's, it's great.

But, um, with the investors, like, they're gonna be the people who are gonna put pressure on you if the business is struggling, right? Or you hit tough periods. Um, and so you, you wanna make sure that these are people who will act with empathy again, because obviously their, their interests are to maximize the returns. But you know, that, that you can do it in a thoughtful way and you can do it in a way where you're helping the business and trying to navigate the difficult times in a productive, constructive way rather than just like, you know, oh, you can't figure it out, like, okay, we got to replace you right away, right?

Right, right.

And, and, um, and, you know, the, the empathy frequently comes from the ability to understand, like, operationally what the company is going through, right? So, so that's one aspect, was like how well the investors understand the operational execution challenge is one. And then the other, I would do the diligence. I would talk to other CEOs and I would specifically ask the investor, like, can you introduce me to a CEO of a company that went through a tough time or that didn't make it? And the answer, like, if people avoid it and, you know, they give you like a fake reference of somebody who kind of was going through tough times but not really, like, that tells you something. Because the reality is that most most of the portfolio investments of the VCs don't make. They have a lot of people to introduce you to. That's true.

That's really true.

You know, that's plenty of people. Overwhelming majority, right?

Right.

So, so that tells you something. And so yeah, I do that and I talk to people. I was like, how was it? You know, and like, and people tell you, even people kind of went bankrupt, they tell you like, hey, you know, we didn't make it, but I felt like I had the investor had my back and like it was in the best interest of the company. And even sometimes like when people got replaced, still it was done in a high empathy way.

Yeah.

And kind of they led them to it and, you know, yeah, it's hard. Obviously it's hard.

Well, so have you ever gotten a reference on a VC, on an investor, and that information said, you know what, we're not going to do, we're not going to go with that person?

Oh yeah, you have.

Absolutely.

That's the thing that happened.

All right.

That's really, totally. And then that really was a signal. Like what, what's an example of something you heard that was a signal that we're not gonna go with you guys?

Well, it, you know, a little bit what I, what I just said, acting with empathy and how understanding and how, how sensitive, uh, the person was like to learn about the situation rather than like make brush, you know, recommendations and like, oh yeah, really need to restructure. You really need to like, if People, if you want to give advice, like you need to take the time to learn about the situation.

Yeah.

Because otherwise it's like, yeah, high level, you don't have the context we talked about. So that was one. Yeah, that was a big one.

Yeah, that's a great example. You know, the life of a startup founder, as you know, is ups and downs. They call it a roller coaster for a reason. And My understanding is that you used to have a mood meter. 'Cause you're an analytical guy, you're an empathetic guy and also analytical. Tell us about the mood meter.

So in the early days of Productboard, I, because I am an engineer by background, I would plot in a spreadsheet, I would basically rate my emotional state on a scale 0 to 10. And the scale was like, the highest was, oh, this is the best. This is the best thing ever and this is gonna change life of everybody on Earth. And then Zero was like, oh, we're not gonna make it, right? And like, we should just like shut this down immediately. What am I doing with my life? This is ridiculous.

Yeah.

And I would plot it, uh, then I would do it 3 times a day, morning, noon, and afternoon. And then I would plot it and it was like a roller coaster. It was like up and down, like sinusoid, you know?

Oh, you actually saw the roller coaster?

Yeah, I did see the roller coaster.

That's fascinating.

And you know, I don't know why I did that. Maybe it was a coping mechanism to understand and like, kind of like see it and be reminded of that roller coaster. Because if you're high, it's easy to forget the lows. And if you're low, it's easy to forget the highs. And so it was my kind of a very scientific approach to remind myself. And it's like, it's really, you know, in the early days I use this analogy. It's like, it's almost a little bit like you have this baby like the startup is your baby and you're walking around the world, you're showing it to people and some people tell you, "Oh my God, this is a beautiful baby, like congratulations and it's gonna be so smart and healthy and everything." And other people show up and they like bluntly tell you, "Oh, I'm so sorry, the heart defect and the lungs underdeveloped, like the baby is like, I'm giving them like 5 days of life." And that's how I felt. Like, you know, I have kids, like, I, you know, obviously it's exaggerated, right? Because it's the worst thing that can happen to you, like, with a child. But you are really so vested and invested that, yeah, the highs and lows are high. And it's, you know, it never— it changes and it doesn't. It changes in the sense that you become resilient and, you know, the sinusoid still exists, but it's much flatter because You've just seen stuff. You had to fire people, you had to overcome challenges, you had all the highs of successes. And so you become a little numb, you know, to the highs and lows. Yeah. So it hardens you.

Yeah.

It's, and it's like everything in life.

Yeah, definitely. Just, just exposure to it.

Yeah. Yeah.

And I think experience, and I would also say, and I'd like to hear what you think about this knowledge that you can overcome challenges.

Yeah, I mean, I think it's a great way of putting it. Like, you know, when you see that you've been through this tough time and you're in it and you feel like, oh my God, this is the end of the world, and then it isn't, you know, and in retrospect. So if you learn to put yourself into that state of mind of like, hey, it's like, what can happen? Like, you know, kind of put it in perspective. I mean, that's like, I had a coach, right? And it was like, put yourself, there's this exercise, like think that you are on a balcony at like a ballroom, right? It's like put yourself up on the balcony and like you watch yourself and everybody else dancing on the ballroom and it gives you the perspective. And I'm sure that you, you've heard other techniques, right?

Totally. Totally.

Um, anyway, it's, you know, yeah. Cope with it.

Yeah. Cope with it. Well, I'm just curious what happened. So I understand that your, your in-laws were, you You're married, you have 2 kids, as you said, and your in-laws were like not so psyched about you being an entrepreneur. And not only that, but your parents themselves were like, "Hmm, not so sure." And I'm wondering how that affected your mood meter.

No, it's not. Yeah, I mean, you know, it's again, this is like simplistic, right? But there was a situation where my father-in-law talked to me about taking care of the family and making sure that financially we're all set because it was a situation where So I quit my job, right? I was eating into savings that I made. This is pre, pre any funds raised. And my wife was actually changing her career. She was getting her second master's. And so she was a student and she had a student loan and we had a kid. And so it was like, young man, like, are you gonna take care of this family? Like, you're doing this startup thing. It's cute.

Yeah.

Like, I wanna make sure that the family is sound and you know, being taken care of.

And did that, how did that affect you?

It's a reminder of the urgency and it's a reminder that you are not in it alone. And as much as, you know, you might be stubborn and committed and kind of like, this is what I'm doing, there are other people around you that are impacted by it. And you can't ignore it. Or like, you know, there's a limit, right? So that's the kind of like, what's the pain threshold? It's not just you as an individual, it is the personal life as well. And you know, like sometimes people tell me like advice for people and stuff like this is a big one that I've learned that it's not fair to put the stress on your loved ones. And, you know, I failed at it so many times because like, who do you talk to? Right. Especially as a CEO, as a founder, early days, it's not like you have the developed, you know, networks of fellow CEOs yet and so on and so on. So anyway, so I would give that advice, like be careful or like, you know, be sensitive to it and act with empathy for the other people around you because they have their lives and yeah, they love you hopefully. Yeah, but it's still, you know, on an individual level, you shouldn't be so self-centric to ignore them. Yeah, so sensitive.

Yeah, I think that's really important and people don't talk about that. You actually, it's important to have the conversation with your spouse, maybe with your parents if that's, you know, it depends on who your family situation is, to tell them kind of in a sense what it's going to take. I mean, you may not know what it's going to to take, but it's important to have the context, be able to sit down and have multiple conversations, because it does— it's not just affects you, it affects people around you. And I think that's powerful. You know, another thing that you— not all startup founders also have kids, and I'm curious, you actually have 3 babies, right? You have your child, right? 2 children in your startup, right? Yeah, exactly. 2 don't have an exit strategy, I guess. Just, just one does. So how do you balance your time, think about that? I mean, not all founders do, and I know that founders make sacrifices in service of their startup, but how do you think about that balance?

I, again, it's hard, it's difficult, and I did some like very like process-driven things, like I blocked time on the calendar. I did make a conscious decision like allocating the time so that I don't feel constantly constantly frustrated by like, oh, I'm cheating on my family, I'm cheating on the business when I'm doing the other.

Yeah.

And so like having that allocation and the allocation honestly is gonna, you know, it fluctuates over time, right? Like right now I'm here in Lisbon for a week, then I'm going to another couple events. I'm gonna be in Zurich and it's like, yeah, the family is gonna struggle, right? Like my kid just woke up yesterday, my wife told me with a fever, and she's now with 2 kids, and I'm sure the second one's gonna get it. So it sucks, right? But anyway, so like having that perspective and having kind of like, uh, almost like a contract with yourself that is as specific as possible so that you know where the balance is, you know, that, that helped me. Um, yeah, and then talking to your partner frequently and like setting the expectations. And like I said, like, you know, it's, I mean, you can make, you can, it's hard. Like I was at a dinner with John Chambers who was the famed CEO of Cisco.

Yeah.

And I asked him this question, like, hey John, so you're a father, like how did you balance this? And he looked at me and said like, unfortunately I wasn't a good father. And he had that, Obviously reflection and so on, like, you know, now, I mean, he's very successful overall and he has a healthy family, but he made some of these sacrifices. And so that's an individual decision. And sometimes you don't see it, you don't feel it when you're in it because the business is always more urgent because the timeline is shorter. And humans, we, it's like whenever it's the long-term thing, Like we always say like, oh, we can do it tomorrow, right? Like getting in shape, losing weight, you know, learning another language, like whatever it is, it's like, oh, you know, whatever, I'll do it. And so I did that. And I also like for the year, I have a calendar, I have goals for the year. And then I translated and I actually have a spreadsheet because I couldn't find a calendar where you would have, I don't care about month, I care about weeks and weekends and where the holidays are. And like, and I, you know, it's kind of like a rectangle thing. And so I plan the time and I look at the balance and what I wanna do personally versus business-wise on the, on the big picture, from the big picture.

Yeah.

And that, that serves as a reminder again, like, hey, like there are the goals, the personal goals, like go visit a new country or, you know, save up something for your family's college. Like, you know, all these things and just keep reminded. And I did even put a poster on my wall. There's this post like 40,000 Weeks, just like every little dot is a week in life based on life expectancy. Right. And I would, you know, um, like put, like I would fill it out and then I would put stickers whenever there was like something great that happened in my life, like getting married and kids and like, you know, some, some major milestones just to be reminded that the life is short and that I need to balance it because if I just focus on the short-term business stuff, like all the personal stuff is gonna— I'm gonna miss it. That's good. It's very nerdy.

Nerdy but effective. I think it's very powerful. You know, I think some— sometimes people don't do that kind of thing because they need permission. Like, it's like kind of like you said, it's a little nerdy thing to do. It's kind of very detailed. And yet without those kinds of reminders and support systems, we just miss it. And so I appreciate so much that you shared that with us. And I appreciate that you do that. I think it's probably very helpful for you.

Yeah, everybody, I mean, you know, I guess different people are different, right? Like, whatever works for you. It's just like, think about it. Like, you know, act. I'm sure that in your book and in the people that you're interviewing has variety of advice how different people cope with it, right?

Yes, for sure. And I think that's— it comes back to be intentional, be aware and be intentional. So just a few more questions for you, Hubert, what is one of the strengths that you think you bring to the table, your strongest strengths, and what's a weakness you're working on?

Um, well, I, I'd say that I— speaking of empathy, like, I do think about others and, and, and how the actions impact others. Um, I think I got it from my mom. Like, she always deeply cared about people, and she would be friends with the front desk people at the office building and she would know all the janitors because she would work there at long nights, but she would actually talk to them and get to know them because she respected them as people that are part of what she was working on in a different role. So that empathy is one. Challenges, you know, I'm very analytical, which is both And I know they call detail-oriented and perfectionist, which is like on one end. Wow. That's quite one, one end, you know, positive. On the other, it's so potentially destructive if you're like never satisfied with anything because, you know, people feel that. And so it's like my leadership team, you know, they, they, they challenge me on that all the time. It's like, oh, there it goes. Negative Hubert again.

You know?

And so like not a nickname you want.

Yeah.

I, I, I did read this book called Positive Intelligence. Recently, and it kind of helps you score like where your weaknesses and strengths are. And so this was one, um, this, this is a big one for me. So I'm, you know, I'm grappling with it. It's, it's ironic though because like that's what pushes me forward as an entrepreneur. Yeah, this is like, how do I improve things? How do I— how am I not satisfied with the status quo? How do I see the opportunity to do things? It's just the balance between too much and too little.

Yeah.

Never black and white.

Yeah. And a constant dynamic balance, right? Sometimes you win, sometimes you lose.

I hear you.

Um, what do you wish you had known earlier on your journey?

Um, a lot of the things that we talked about, about people and scaling companies and the challenges and the leadership. Um, I wish I knew like what is important and what isn't. It's just like at the beginning of the start, so I, you know, I would spend time writing contracts myself, or, you know, I would be cheap spending on lawyers and just like the delegating, like I wouldn't be delegating enough. And you're trying to do things. And again, that comes to my perfectionism, you know, things that wouldn't be the most important things impacting the business in the fastest way. And so I wish I didn't do that. I wish I spent extra dollars on a really good lawyer. You know, I wish I delegated more. I wish I raised money sooner. It's like I did push the family through like, you know, very tough times as a result and stressful moments. And I don't know, it's always a balance because, you know, then the investors are like, oh, we're really impressed how frugally you can operate, right? And how far you got with no funding or like very little, you know, spend and so on. So it's always, it's like a coin that has two sides. And then the personal, on a personal thing, maybe one point is careful with your friendships and your business, you know, because there's a high chance that you're gonna ruin your friendships over the business relationship. So what I mean by that is that, you know, Founders, it's unique, right? But then later on when you're employing people, if you're successful, you will have friends who will want to join you because, "Hey, you're building successful business," and so on and so on. But then if you fire them, again, not because like they're terrible performance, but because the company outgrows them and you don't need the role anymore, it impacts the friendship.

Yes.

And so I don't like it. Just like, you know, I lost some friendships because I've done this and I, you know, I wish I didn't because it was not worth it. It's just, yeah. Anyway.

Yeah, I hear you. That's very powerful. Thank you for sharing that. My last question is, what advice do you have for other founders as they embark on their journey to grow into leaders?

Leaders? I'd say, you know, find mentors that are not necessarily mentors in your space. Not everybody needs to be like a CEO, founder in your category and so on. Like one of, some of my most impactful people in my life are people in their 70s and 80s from completely different industries. Like they've never done anything in startup tech, but guess what? The psychology and, you know, the dealing with interpersonal struggles and That's like, that's not new. That's like, you know, humanity, the skills and the wisdom and the experience that you get from being around people and solving conflicts and so on. So like find those people who have the wisdom, who have the maturity and talk to them about the personal things. Yeah, they don't have the business contacts, but on a personal level, like they will help you empathize, they will help you see you did from other people's perspective, right? So that was a big one for me. The other one I do want to reiterate, like, think about your loved ones, the impact there. And then, you know, as you're building the teams from the leadership perspective, like, try to have these— set the expectations up front. And, you know, even for founders, I mean, you hear about all the time, like, have the conversation. Everybody should be vesting, you know, the equity. It's not that you split it at the beginning. Don't assume that this is a marriage forever for all the people. It's not like for the founders, it's hopefully gonna be the longest lasting one, but, you know, set the expectations.

Yeah.

Yeah, that's what I would say.

Well said, Hubert. Thank you. This has been such a fantastic conversation and so much wisdom shared. People are gonna really benefit from it. Thank you for joining me. I really appreciate it.

Thank you for having me. It was wonderful.

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.