#23: Scott Belsky, Behance

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 23, and what an incredible one it is. Today I am talking to one of the greats. Scott Belsky. Scott co-founded Behance, which is an online platform to showcase and discover creative work. Scott was the CEO from Behance's founding in 2006 until Adobe acquired it in 2012. In addition to being an entrepreneur, Scott is an author, an investor, and a self-identified product obsessive. He's currently Adobe's Chief Product Officer and Executive Vice President of Creative Cloud. In addition to knowing firsthand what it's like to go from startup to grownup, Scott has mentored, advised, and invested in many entrepreneurs. So he's a ton of experience guiding others. He also wrote an incredible book, The Messy Middle. Everyone should read this. It was incredibly inspiring to me when I was writing my own book, From Startup to Grownup. This discussion is filled with nuggets of gold. Scott talks about how he knows he can trust an executive. Why he sees culture as an immune system, and why it's important to extinguish most new ideas. He talks about how he's grown as a leader through stress and strain. So those of you going through stress and strain, please know that you're growing as a leader. And how he does retros on his leadership after he makes mistakes. We talk about the pushback he got when he brought in the first COO of Behance and how he got his team through it. And listen up. We talk about the secret to motivating people. This episode is filled with a ton of super practical advice for founders and all leaders. So grab a notebook and please enjoy this incredible discussion with Scott Belsky. Scott, welcome to the show. I'm so happy to have you today.

Good to be here.

You know, I wanted to start, you know, you're well known as a designer, of course, and you know, someone who loves products. And I'm so curious about if you think about yourself as a CEO when you were a founder and a CEO, how building your skills as a CEO is like building a product.

Yeah, no, it's a good question. You know, I, I feel like product is one of the most human disciplines. You know, you're ultimately building an experience for people, taking into account their natural human tendencies, their desire to look great, you know, to do more in less time. There are, frankly, a degree of laziness when we're first doing something for the first time. And we don't have time to read tours and go on crazy onboardings of products. We don't want to endure learning curves for things we don't even know we want yet. Really, it's an empathy-driven discipline, designing products for people. And ultimately, the better you understand people, the better those products will perform. I think leadership is quite similar. You know, when you're ultimately building an organization, you're doing so based on the desires and your understanding of the tendencies of people. And, uh, you know, pragmatically, like, what are they worried about? What are they insecure about? Why are they here? What chips on the shoulder, you know, drove them to take this risk in their lives, in their career? And, you know, understanding the makeup of, uh, of the organization is very similar in some ways, to your point, uh, to building a product.

Yeah, I, you know, I love the way you put that. And I heard you say in another podcast that, you know, leadership or management is not scalable because at the end of the day, you're really working one-on-one with that person trying to unlock who they are.

Well, yeah, I think that I always like to say to entrepreneurs, I think that the best new products are remarkably unscalable in the beginning because you're trying to get a really tight conduit to the people and to what they're feeling and how they're going through it. And, The best way of doing that is to not try to automate and scale everything from the onset, but to really be in touch with the customer so you can understand the pulse of how they're dealing with the product and what's working and what's not. And yeah, one of the joys of building a company is you go through every stage. And when we were probably up to our first, I don't know, 50 to 100 people on the team, We, uh, you knew everyone's name. You could actually kind of control and feel the immune system always, you know. You knew when the team had a cold, so to speak, and you knew when to have an intervention. And then at some point, it just gets out of your hands. And, you know, now overseeing an organization of thousands of people, you know, there's no way I can handle or know every day who's insecure about their career, who's on their way out, who's on their way in, like And I, you know, you have to find new ways of doing it and it ultimately relies on other people. And it's hard to make that transition from being self-reliant, which you have to be as an entrepreneur, and wanting to sort of control every aspect of the, of the closed system of building something, which is really a helpful thing to do until it's not.

And actually, just, just to key off of that, how do you make that leap? What advice do you have for founders and what advice do you give to founders about making that leap kind of from the first 50 to 100 where they're hands-on to the point where they're managing thousands of people where they cannot be hands-on anymore? Like, how do you— what's the best piece of advice you have for them to do that?

Well, I think you look at, you look at all of the leaders on your team that are overseeing the various functions or products, and you have to believe that each one is someone you can really trust, someone you can trust to represent you, someone whose judgment you trust, you know, you start to feel like they don't need you, and that's a good sign. When you feel the opposite, when you feel like you have to validate everything and you don't want to actually introduce them to the customer because you're a little embarrassed and you don't want them to meet that new employee you really want to hire because you don't think they'll sell them well, and, you know, you gotta like tune into those instincts and say, all right, this person is not going to be successful here, and you have to, you know, part ways for their benefit and for your benefit. But it's, it's ultimately about at scale It's about finding and sufficiently empowering and being able to trust people. And that's one thing I've learned maybe the hard way because you jump in, you think you can fix everything, and it doesn't work that way, especially as you get scale. It's more about finding the right people and then knowing what questions to ask and what gates to set to ensure that they're the right people.

Yeah, and what trust looks like. I was just having a conversation today with the CEO and the idea that part of the goal of the executive or part of his expectations for the executive team is that they build trust all around them, including with him. And that was like a concept for him, a new concept for him, I would say. But that's really what you're talking about, that you have to really trust the people who are empowered to act for you.

That's right. That's right. And you have to give them the time and go through the motions. To be able to build that trust. Right. So, you know, for me, it's strategy sessions and offsites and building a strategy together and having that leader lead the meetings with the people that are— and see them, see him or her drive alignment. And really, you know, you start to get a feeling after a series of these meetings, okay, this is in good hands. I'm going to now focus on something that's not in such good hands versus, oh, this is not going to— you know, I need to micromanage this.

Yep, yep, totally. Now, I want to touch on something that you already referred to, the idea of the immune system.

I love—

I just heard recently you talk about that. Talk about when you say culture is an immune system or when the team has a cold, what do you mean by that? And what can CEOs take away from that?

Yeah, well, a really well-oiled organization rejects anything that's new. By design. And that's helpful. You know, the way to keep focused is to extinguish new ideas, most often quickly, right? Um, you know, that's how our bodies stay healthy, is that we reject all the foreign DNA and viruses and bacteria and everything, and we stay healthy. And 99% of the time, that's exactly what you want. And how do you have that shared set of values and principles and practices? And, you know, people that are empowered to, you know, veto a new candidate that you're hiring, or veto a new idea that came up, or you know, in a comfortable, healthy tension in the, in the leadership team, you know, is always critical to that strong immune system. But occasionally you need to blunt the immune system and allow a new organ to take hold. You know, that's what doctors do. They suppress your immune system so you can get an organ transplant. Hopefully not often, but when you do, it can come in the form of a new senior hire or a new part of the product, you know, a new product that changes the way you organize your business. And to be able to suppress the immune system is hard. And I remember, you know, one of the most critical hires that I ever made for Behance was our first real chief operating officer. And he came in with his own history and background and best practices. And, you know, in the first 2 or 3 weeks he was on the job, people were basically, you know, lining up to get into my office to tell me how this person wasn't going to work out because he wanted to call meetings this way and not that way. And because he was measuring things differently and, And I had to realize, I had to say, listen, we have to give him 3 to 6 weeks to like, really, let's take his lead. And we can always reject and return to the previous version after that. But let's really try. And lo and behold, he became the most critical hire we ever made. He transformed the business and actually led Behance for many years after our acquisition. So I think that's the story, right, is the immune system is an important thing so long as you know when to suppress it.

Yes. You know, Scott, I love what you just said because, of course, well, we well know we bring senior executives in, we call them organ rejected if it doesn't work out, and we try to coach them to fit in with the team. But how do you as a CEO feel when people are lining up to say, "That guy's a problem. I don't like the way he's doing it. I don't like change." How do you as a CEO handle that? Because it's possible you made a mistake, and I've seen many CEOs who've made the wrong hire, but I've also seen CEOs not be able to withstand kind of the, you know, the rallying of the troops. So how did you think about that?

Well, I think it would start by saying, you know, here's where we're struggling as a company right now and where we need to change and scale. Let me help you understand what's going on. We need help. We need someone with the qualifications, the background, who is empowered to do X, Y, and Z. You know, this is why we hired this person. They, you know, this person has a background in this, background of that. She got great reviews and references on this or whatever. You know, you help them understand the decision. In order for this person to be able to improve our organization, they're going to need to get a ramp-up period of time where they're not being judged. You know, it's funny, we spend so much time hiring talent but so little time grafting talent.. And it's just as hard as hiring talent.

I think it's harder.

Yeah, it's probably harder. So let's, let's figure out like, how do we, how do we set this person up to succeed? Now, if we do everything we can to set them up to succeed and they don't, we will move on. We will make a change. But it never, you know, a critical hire never feels great at first because too much, you know, they're, they're gonna, they're, they're so experienced, they're gonna come in and change things like right off the bat. And You know, again, like, we, you know, we don't like change, as you said. And, you know, I always go back to Seth Godin's lizard brain, you know, the ancestral part of our brain that makes us cling to the familiarity and run away from all sorts of newness. Familiarity will not get you to where you need to go. It'll keep you where you are. So I think that would be the logic, you know, path I would share with, you know, someone who came in and have that conversation with me. And I would make them feel the responsibility to help this person be set up to succeed.

How about you yourself? How would you kind of check in with your gut and with this person to make sure that they're operating as expected and there aren't actual red flags that the people are bringing you?

Well, I think that first of all, the red flags I'd be looking for in the early stages are values, a lack of curiosity, a lack of asking questions. Reminding people they're here to learn for a period of time and to gain the credibility of their teams. And that's why I think an experienced person who's good at grafting themselves onto a team comes in and proclaims their ignorance, really wants to ramp up and understand and learn and ask questions. And then once they start to formulate a strong opinion, they start to check it with people and then get guidance on how to act upon it. I think you want to look for red flags or people who are skipping those steps because then they won't succeed.

Right, right.

I love that.

That's a really well— that's really well put. Now, Scott, tell us about your own leadership journey. I mean, you know, you started as a founder and you were bootstrapping for a while and you grew that company all the way and then you got acquired and now you're a senior executive in a big company. What are some of the things that come to mind when I ask you about kind of your transition points as a leader? What are some things that come to mind that really stand out for you as your growth as a leader?

Well, I think that growth as a leader comes through strain and stress, at least for me. You know, I actually don't get much out of— I mean, I get some confidence out of the things that work or an acquisition or whatever else. But the true growth is like, you know, the muscle tear, right? It's the stuff that doesn't go so well. I think having to kill products before and wondering, why didn't I kill this 2 years ago? Having to let people go and see the organization suddenly breathe again and asking myself, why didn't I make that decision faster? And then trying to really always force myself to kind of understand why. Yeah, I think teams do have a tendency to kind of move on when something is killed and they don't really do the retrospective. And I love doing that retrospective. I think that sort of insight is truly up-leveling, I think, in a career. So, I would say it's largely those periods of strain and stress, leading through a downturn in my startup that I had and really you know, getting pretty close to running out of runway a few times. Yeah. And then, you know, seeing how the market reacts to things and seeing what ends up making a dent and what doesn't. Those are also teaching moments.

Yeah, for sure. When you do a retrospect for yourself, is there— do you have a formal process that you do when you sort of think about your own leadership?

I don't. I just— I think I just get super thoughtful and self-critical. And, you know, I say to myself, okay, no one's listening to my thoughts other than me right now. So I can go all out, I can blame myself in any possible way, no one has to know. So it's a safe space in my brain. What did I do wrong? Why did I hesitate? Why was I scared? What was I worried about? What signals did I miss? And really just, I think you have to be very critical in that way. Just like a great product leader is never fully satisfied with his or her product. You also should never be satisfied with how you conducted things. Like, if you made a tough decision that should have been made earlier, call yourself out on it. You just robbed the team of another 6 months to a year of the sensation you're getting now by finally making that decision. Like, understand why.

Yeah. I had Paul English, the co-founder and CTO of Kayak. And he said, it's like, as a leader, I make a contract with the employees that we're going to create a certain kind of place to work. And then if I keep an employee around for too long, I've kind of violated violated that contract. So, I like the idea of the way to think about it. Have you personally picked up patterns in yourself as you've done those retros? Like, why do I, what am I scared of, or what do I put off in terms of difficult decisions?

I think my general weaknesses track back to being a bit too optimistic in the power of a product or the power of people. You know, and I meet people and I want to see like what they could become. And I want to tell myself a narrative of what they're capable of and, oh, they could do this and they could do that. And in doing so, sometimes I actually forget to ask the right questions to validate whether or not this is the case. So I catch myself, you know, I think that some of the mistakes in the past have been made, you know, based on, based on, based on those sort of assumptions that should have been validated more rigorously. And, you know, and Once you though, like, face that, then you start to make little tricks and rules for yourself. Um, or you find other people who can compliment you, you know, and I, sometimes I go to someone else who I know is very different from me on this and I say, okay, you, you meet this person. Like, I wanna hear what you have to think.

Right. So getting it validated from somebody else. Uh, can you share maybe one or two tricks or, or decision rules that you've created for yourself that help support you?

I try to leave time to think about things, you know, even when you're so sure in a meeting that you want to hire this person or you want to make this decision or you want to move this around. I really force myself to have some period of time to think on it because, again, I know I can get like high on the efficiency of making a decision and I want to make sure that that doesn't influence my reasoning. I would say that's one of them. I think the other one is I will always say to myself, who else from the team could add value to this? Again, I'm so into expedience that I like to just kind of push things forward. And I will often be stepping on toes if I do. So I want to make sure I consider empathetically, who else's shoes could I be in where I would want to either have a say in this or be able to challenge me on this or be able to weigh in on this decision? Who are those people?

Yeah, that's great. Now, Scott, you are one of those founders who, you know, you grew your company and then you got acquired. And then I have to say, like so many founders, they get acquired, they stay with the company for 2 years or 4 years or whatever it is, and then they leave. If I'm not mistaken, you left Adobe and then you came back. So now you're like a senior executive in a large company. Tell us about the difference between, you know, being the founder and being the leader of your growing startup. And you're actually a full-grown startup as compared to being an executive at a large company. Like, what are the kind of the pros and cons of each of that in terms of leadership?

Yeah, well, I think that, I mean, obviously the biggest difference is again, that degree of control you can have over the— it's a closed system versus an open system. And I, you know, I miss the sensation of a closed system where I can just— everything from the office and the space to the policies to the slide deck and the style of the slide deck, to the people we're hiring, to the food that's served. Like, I can have my touch on everything and really like have a closed system experience that is very special. You know, there's something very special about that. When you get to a huge company, a lot of this is out of your control. I mean, you might get one email saying, hey, what do you think about this office renovation? And then like there's a whole team that's staffed on that and, you know, they can't involve you in those meetings because you have a million other meetings to be in and And so you have to— it's an exercise in actually letting go of a lot of things and really forcing yourself to focus on the few things that you can do that move the needle the most. And, uh, you know, I think it's a very healthy forcing function that I've had to go through. It's teach— it's taught me quite a bit about how I can add the most value. But still, you know, you, you sometimes look at something that happened, you're like, oh, how did that get out of my, my hands? Like, that's not the way I would have wanted that to be. And so there's a lot of that compromise. And maybe that's why the bigger the company, the more inconsistencies there are across the customer experience and the brand. And it's just, you know, you can't have one person at the center of all of it. So, so I think that's, that's like the daily drama.

Yeah, the daily drama of, of I think also being in meetings and working cross-functionally. I mean, you must have to really learn how to, you know, navigate and deal with your peers cross-functionally in a way that you just, just wasn't part of your ecosystem at the startup.

I think that's right. But also, you know, the tendency as an entrepreneur to resist the status quo and change new processes and ways of doing things. I mean, those are all— those all pay a premium in a big company. And so those of you that are entrepreneurs listening that have the tenacity to like make that happen in a bigger company against the grain, it's really exciting.

Yeah, yep, totally. Now what I appreciate about you, and certainly in your book and on podcasts I've heard about you is that you're so honest about what it's like to be an entrepreneur and the ups and downs and the brain space it takes. And I guess I would love to hear maybe if you could just share one or two of your like most nerve-wracking moments as a founder, maybe to give hope to other founders who are going through massively nerve-wracking times, nerve-wracking things, especially in this time with the economy.

There are many nerve-wracking moments because, you know, startup is a very— it's always in a delicate balance. You know, you're always— you're running more on hope than facts. You're working amidst complete anonymity, oftentimes ambiguity, uncertainty, and anxiety, right? And you really just don't see an end in sight. You tell yourself this great narrative, and then you, you know, you walked out, out the street into the corner, and you realize that the guy selling fruit on the corner has a better business than you do. Um, and, you know, it's sort of humbling to realize, oh wait, like, I'm losing money still, this is not viable, and our default is debt. And, um, so those are, you know, that's all— those are all very, you know, tricky, tricky things to stay excited about. Um, I always like to say that leading a startup team is like driving a car cross-country with the windows blacked out in the backseat and everyone in your team in the backseat. And so they're all wondering, like, where the heck are we? Like, why is our car not moving? Like, why are— and what you can do as a leader to not make them drive themselves crazy is to narrate the journey for the people that are in the backseat that can't see. Right? So we're crossing state lines. Oh, we're in some traffic now, but I see it opening up. You know, you, you, as you tell the narration and you merchandise the progress that you're making to the people that are making it, um, you can actually keep people engaged, you know, through this very, you know, volatile period, uh, that I like to call the messy middle. And I think without, you know, without that, it's really hard. And that's why You know, attrition is really bad in the startup world and people are always attracted by headlines that suggest that it's better somewhere else than it is where you are. Well, my story is that I think the competitive advantage of great startups is sticking together long enough to figure it out.

Yes. I mean, that's so wise, sticking together long enough to figure it out and being able to withstand all that, all the ups and downs and something you just said. You know, I really loved your book, The Messy Middle, and I took away so many things from it, but the crowning thing I took away was this idea of merchandising progress. I loved how you put that. Could you talk more about why that's so important? And why also, I know you talk a lot about progress and the motivation of progress. Could you talk more about that?

Yeah, sure. So when I was getting my MBA, I studied under a woman named Theresa Mobley at Harvard Business School who did a lot of research on motivation and creativity. Enterprise. And she did this big journaling study, and, you know, long story short is the realization was that people felt most motivated, um, and made more progress when they felt they had made progress. And so there was a bit of a chicken and egg thing associated with progress that I found very fascinating. Um, my second point would be that the— there's a, you know, $100 billion plus industry called advertising that all just makes stuff that merchandises actions to us, right? And so much of our consumer behavior is determined by the ads we see, the billboards, etc., that get us to do things. And so I think you kind of have to use those same tricks and tools of merchandising to help people understand and see the progress that they are making. So, you know, I would like to advertise to my team the progress that we are making using the same tricks of advertising, like clever, pithy stories and headlines and beautiful graphics and very convincing narratives so that people can see, like, we are making progress even though it doesn't feel like we are and no one knows who we are yet and we're not making any money. We actually are progressing. And when you leave that, you feel motivated to make more progress. And I think that's the responsibility of the leader.

Yes. How would you say the leader should motivate him or herself and merchandise progress to him or herself?

Yeah, I know I am— for me, it's writing. You know, I like to write letters to my teams. I like to explain and remind myself as well as them, like, why we're here, like, what we're doing and why this is important work and the opportunity that's in our hands, you know, to seize. Writing that out is a part of my cathartic processing and churning through what our next steps are as a team. So I think writing is important. And I also think setting annual goals for yourself is important as well. I used to make a list of kind of the few things that I just wanted to end this year saying I had done. You know, some of those were things for the team and our culture. Some of them were key hires or, and other, and others were just product milestones I wanted to have us achieve. And it's really fun when you look back the year, you know, a year from then and realize, wow, like we did most of these.

Yes. Setting goals and achieving them. To your point about progress, there's like nothing like that. Yeah. You know, I had Rahul Vohra, um, the, the founder and CEO of Superhuman on the podcast and he, told me that when he pitched VCs, you know, they would go for funding and he would pitch VCs or he would just like have conversations with them. It was almost like he got re-energized. So, he felt like every 6 weeks he has to re-pitch himself to remind, to keep himself, you know, up to date on motivation.

I think that's a great point. I mean, listen, you're always selling in this job. Yes. You're selling employees, you're selling investors, you're obviously selling customers. And you're selling to employees that you currently have to retain them.

How do you manage right now your own personal and professional development? Like, and how has that changed over the years? Because it seems like you're someone very interested in self-growth.

In terms of self-development, you know, there are a number of people that become mentors of mine that I try to check in with, you know, once a year, plus any time a major decision, you know, is on my mind. Those people play a key role for me in my life. There are also key people on my team that I really deeply trust, that I want to run certain things by and ask for feedback. And oftentimes when I do a big all-hands or whatever, I will usually ask a few colleagues, you know, what could have done better? Like, what didn't come across well? I have a wonderful chief of staff, a woman named Emmy, who will always tell me, you know, you spoke too fast or this part didn't really click with people or whatever. And I think that's invaluable feedback for me. By the way, when you ask people for feedback, then they feel compelled to ask you for feedback, and that's an opportunity for you to give them feedback. So it's a great, it's a great tool to use, you know, with your team.

That is so true. How do you as the leader and how do you— how did you as the founder CEO and now how do you as a leader really get people to tell you the truth? Because it sounds like you have some trusted relationships where you've built up that context, but you need a lot of people telling you the truth. How do you think about that?

Yeah, I think I would say that my biggest struggle is with people who I don't think tell me the truth. And usually it's because they don't want to disappoint me, but it's, you know, it ends up backfiring. So I think it's important to make sure that there's a safe space to build relationships. And, uh, you know, I, I think I can sometimes cut steps there because I just want to kind of get into it and get things done. Again, I'm always optimizing for efficiency, and you can't, you know, sometimes you just can't fortify a relationship super quickly over Zoom. You know, you just have to spend time with people. So I am, you know, recognizing where you, where and when, where you can and can't take shortcuts, I would say, is, uh, is critical for that.

Yeah. You talked about mentors. Can you tell us how you've kind of gotten your mentors and specifically what kinds of things they help you with? And you can feel free to mention names if you would like, but you don't have to.

Yeah, no, I mean, I have my mentors, you know, I have one person who's just a really legendary product leader and builder who has always sort of You know, whenever I say things to him, he knows what I'm just saying to convince myself of something versus what I really mean, and he has the right questions to ask. You know, I have a couple other mentors that are a bit of like Yoda characters. They're, you know, incredible. One's an incredible designer, and one is a very well-known author who, in the business world, who just, you know, I have a pilgrimage where I visit him once a year, and, you know, he, uh, he challenges me on some of the decisions I have made. And I remember a couple years ago he said, promise me that next year you'll be on planes 50% less. Um, and I thought, that's impossible, absolutely impossible. And then COVID happened.

So I, I'm sure he did not cause COVID.

Yeah, but, uh, now I have to, I have to adhere to that now that the world is opening back up. But, you know, these are people who I really respect and who know me, um, pretty well. And, you know, I, I really value their honesty. I guess one common trait across all of them is they're just completely candid and will tell me exactly what they think.

So I have to assume— I'm positive actually— that you're now a mentor for other founders, and you're also a seed investor. And I'm just curious How has mentoring other up-and-coming founders and others, how has that made you think differently about leadership, or how has that changed your own leadership style, if at all?

Well, it's really rewarding to go through another person's journey in an intimate way with them. It's a lot of fun, as you know, as a coach. It's really amazing to sometimes be in that room and learn from their experience. It, you know, makes me realize a lot of the things I've learned and how they can be useful. Um, and, uh, and I just get a real great sensation from it. I feel like I would also like being a teacher someday, maybe, you know, just that feeling of helping people get to something on their own, and then they synthesize it and they realize, oh, like, they realize what they need to do. And just to play like a small role in that is really rewarding. I also learn a lot because I will say things, you know, in our conversations that will then make me realize the clarity of something that, that I had never framed that way, that I then use with my teams, you know. So that happens all the time. And I think it's probably just having thought partners and other, other people's problems that you can help reconcile, and then you suddenly get an insight into your own problem.

Yeah, that is so true. Is there a common theme If you think about the CEOs and the founders that you mentor, you advise, are there some common themes that come up that you sort of see all the time?

How to hire, you know, how to make sure you have the right hire, how do you change org design, you know, is one that comes up constantly. Is how should I structure this? And the tricky part about that is that it's really dependent upon the people and the nature of the business and the culture and then the strengths or weaknesses of the founder. I mean, there's a lot of nuances. So anyone that tells you that Ching should be either functional or horizontal, there's no rules that you should listen to. And anyone who tells you otherwise is wrong. So it's really a conversation about org design. I would say also getting to product market fit is always a common theme. Should I quit or should I stick with it is a common theme that I go through with a lot of founders. You know, in the messy middle, you know, and then I would also say difficult choices, you know, being in the room with a term sheet for an acquisition and should I do this? Should I not do this? You know, these are all the types of conversations that, you know, that I get to have. It's, you know, I learned from each one.

Yes. You know, that you've articulated so many things that like literally you can't answer for them as in that's a hard thing to know. And it's more of a weighing pros and cons. Are there frameworks or or questions that you find helpful to get them to ask themselves or that you ask them that help elucidate some of these topics?

Yeah, I think I have a framework for all of them, different ones, you know, different framework for each of them. You know, for example, on the M&A front, it's like really around, it's really around the what's best for the customers, what's best for your team, and then the financial outcome within apples to apples for increased dilution and market risk in the future with future fundraising versus now. And I always try to, That last one is a math exercise I try to bring them through. And the former two are more around how they should think about what's best for the customers and what's best for their team. And so that's, for example, a framework as it relates to acquisitions. And yeah, I think there's many frameworks I'll pull into play. And you're right, I don't ever say, I actually try not to say what I think they should do. Because I don't know. But I do try to pose the frameworks and the questions and start to get a sense of where they believe they should do.

Yes. If you think about someone coming to you and say, "Oh, it's not working. Should we quit or should we keep going and try something different?" What kind of frameworks or questions do you have for that question?

Yeah, the key framework for that is around measurement of conviction. And I sort of ask them, "At the beginning when you started this, before you knew anything, did you have a lot of conviction that X needed to exist? And the answer is always yes, right? It's like, yes, you know, we were so certain. And then the question is, okay, regardless of whether you found product market fit or not, let's put that to a side for a minute, because you can keep trying and you can get it the 4th time, the 5th time, or the 7th time. Like, that doesn't really matter. What— it's painful, but it doesn't really matter. What matters is, as you're learning with customers, as you're learning based on what you're showing people and the conversations you're having that you didn't have when you started this journey, have you gained more or less conviction? And they think about that. And, you know, some are like, more conviction. Like, I mean, I know this needs to exist and there's definitely willingness to pay. And then I'm like, okay, this is par for the course. You're in the messy middle, no problem. We have to talk about hacks to keep your team engaged and endure the lows and optimize the highs and stay forward 5 more iterations ahead, stick with it. If the answer is, honestly, conviction is wavering because we're hearing this, but then we validated and it's actually this, and we tried this and people didn't even agree with us, then I have a different conversation. And then I say to them, there's no pride in trying to figure this out. Like, if you're— if you've lost conviction from the moment when you had no knowledge, you know, now with all the knowledge you have, try something different. Like, life is short. There's no shame in quitting. In fact, you're going to leverage what you learned and you'll either pivot or do something completely different. That's fine. Like, let's have an honest conversation about where your conviction level is based on all you've learned.

Yes. And I think it is so hard. I think actually you're doing a lot of service for folks because they need permission sometimes to give up if they're too close to it. And it's not about giving up and quitting because it only gets hard. It's about, to your point, the level of conviction. Has something changed either in your insight about it or also your own attitude about it?

Yeah, in the conviction piece, you'd be surprised how many people keep working at something even though they've lost conviction based on what they've learned. And that never has worked in my experience.

Right. Totally. Now, Scott, you're someone who has a fantastic network. I guess I would ask you, how do you think about, you know, continuing to invest in your network and build your network? And what benefits have you gotten out of having a great network?

Well, you know, I think that my, my whole view on network and networking is that sharing is the new networking. I know when you used to go to cocktail parties and give out business cards and try to connect with people on LinkedIn. You know, I think, I think now the best form of networking is sharing ideas. I've always been very liberal with ideas. You know, I've always been very responsive to direct messages and emails and, you know, trying to make everything like kind of publicly available because then you get— you become known for the things that you've created and or the knowledge you have to share or the interesting questions you have to ask and those are all unifying principles. Those bring people together and make people feel a sense of value from you that they want to then return. So there are a lot of people that are in my network that I've never even met physically. They're just people that I have been following, or, and they've been following me and my ideas for years. And we rally and riff off each other on Twitter or wherever. You know, and when 8 years later I have some question and that person works at that company and I DM them and say, hey, can you help me with this? We feel like we're like best buds, you know, it's, we've gone through so much together even though we never actually met. So, uh, you know, I think that sharing is the new networking and, and that's why I advise people to get active, you know, sharing your ideas on Medium or publishing or, you know, um, posting on social, you know, to people in your industry and following them and, you know, agreeing or disagreeing with their ideas and engaging them. Like, this is how it happens.

I love that sharing is the new networking. I love that so much. I put on a t-shirt. I will credit you. And also, um, you know, as a coach, I'm constantly saying to people, build your brand. But it's not superficial, build your brand. It's really about figure out what you think by writing about it, by exposing it to feedback of others, and by interacting in the world of deals with people, and it both helps you sharpen your own thinking. It also helps you connect with folks you don't even know around you.

And by the way, one of the most valuable things I do every year from a networking perspective is I take a day, you know, at the end of December, and I synthesize kind of 7 to 10 outlooks for the future, things that I am most fascinated by that I think are going to happen, you know, in the near, in the, in the near future. Um, and it's a way of me synthesizing all the trends that I've seen, the things that I— it's a great exercise for myself as a technologist. And every time I publish this, you know, tons of people reach out, you know, this is the business I'm building that's doing this, or you should meet so-and-so, you should meet so-and-so, or, you know, it's just a, it's an amazing like source. And, you know, and I, I wonder like everyone should publish the 10 things that they think should happen in the near future. Everyone should do that. Why not? You know, and people might ignore it for a few years as they did mine originally, and then eventually they'll pay attention and That's a— it's a great exercise.

I love it. That's a great exercise. Okay, we should all do that in December. Scott, just a couple more questions. What do you wish you had known earlier on your journey?

You know, I think that one of the things you have to figure out as you're building a team is the balance between initiative and experience. You know, and I think you want to— early days, you want to hire more for initiative than experience because you're in an environment where everyone's going to have to work together to figure it out together. And there's something really wonderful about that. If you hire too experienced of a person too early, that doesn't have initiative to change and navigate, they won't survive the sprints, they won't survive the pivots and the multiple tries to product-market fit because they're experts. And so they'll want to move on somewhere to somewhere where they get it already. So, I think that hiring for initiative rather than experience, but then you can make the inverse problem later on. When you're hiring to manage a big product and team, hiring for initiative is not enough. You need to hire experienced people who've seen this 10 times before, who can help the team step around disasters and that sort of thing. So, I think that's one thing I have learned the hard way that I wish I had known earlier on. And, you know, and then again, I would say that a labor of love always pays off, just not how you'd expect. I think I've seen that time and time again in my career as well. I love that.

So well said. So last question, what advice do you have for other founders as they embark on their journey to grow into leaders?

Well, I would simply advise people as they're choosing opportunities or job opportunities and that sort of thing, to just ensure that they're getting an incremental step closer to what they're genuinely interested in. And, you know, we're tempted sometimes to take a job because it pays a little more, or, you know, or because it's at a sexy company name or whatever, when in fact what we should be doing is we should be trying to work with people that we really respect and want to learn from, and we should be trying to get incrementally closer to what's genuinely interesting to us. The people that I know who've had the luxury to take a year or two to just be, as my friend Dennis Crowley recently said, like a CEO of your own passion, they end up creating great things. You know, taking that time, I think allowing yourself to be a tinkerer and explore your interests and engage with them a little bit if you have the luxury to do so and can, you know, put enough food on the table to survive that period, I think it's a really helpful thing to be able to do as well.

I love it. I love it. CEO of your own passion. Thank you, Scott. Thank you for your generosity in sharing what you had to say today. And I know people are really going to benefit from it.

My pleasure. Thanks for having me.

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, Alisa Cohn.com.