Founder dynamics

Episode introduction

Episode Transcript

Sam Corcos: I remember distinctly a specific conversation where we had our one-on-one for an hour, and I felt a lot of tension in the call. I imagine Josh probably felt it too. Then I think I called Josh back immediately afterwards and said, “Hey, I think there’s some tension here. We need to talk about this.” We blocked off basically the whole rest of the day. I think we spent the next six hours on a Google Hangout talking about it.

Ben Grynol: I’m Ben Grynol, part of the early startup team here at Levels. We’re building tech that helps people to understand their metabolic health. This is your front row seat to everything we do. This is a whole new level. Having direct conversations with people and giving them feedback is never easy. It’s actually really hard. It gets harder when you start to think about relationships, the emotional side of things. Whether these relationships are personal or professional or family members, friends, it doesn’t really make a difference. Where it gets really interesting is that we, we at Levels as a remote team, we don’t necessarily have opportunities to build in-person engagement and so we have to work really hard to make sure that we’re having conversations that are meaningful on an ongoing basis. One of the ways to build rapport with people is that you have to make time. You have to make meaningful time so that you can have conversations that lead to a place where people feel like their ideas are shared, their ideas are heard.

Ben Grynol: Josh and Sam, the three of us, we sat down and we talked about what it’s like to co-found a company with many people and what it’s like to go from having a personal relationship to actually having a work relationship. How things have to evolve. It’s easy to understand that relationships aren’t a linear path. It’s not just some static line. Relationships oscillate. They go through ups and downs, peaks and valleys with all the different things that go on. A lot of the relationship for Josh and Sam has been built out of making time and really being thoughtful about the way that their relationship is approached. When they have feedback for each other, they take the time to actually get to a place of resolve. Where we started off was some of the backstory, how they met, how their relationship evolved and where it’s at now.

Ben Grynol: What we know is May 2nd … Gosh, I was going to say 2021. May 2nd, 2019, Sam had given you a call because he was looking for some advice for one of his friends about homeschooling and just general overview of it. That led to a conversation around, “Hey, how’s that thing going that we talked about back in August of 2018 in New Mexico?” From there, things went very, very fast. Where Josh, you are in New York basically a week later. From there, fast forward a month to June 24th, 2019, and all of a sudden, there’s this thing called Levels that is a company and it’s incorporated. It’d be interesting just to rewind. How did your relationship even start before Levels?

Josh Clemente: Before Levels, my dad introduced us in, I want to say, 2014. Yeah, about 2014. Sam you can tell me exactly what it was, but I think there was an event going on and my dad is former FBI. He talks a lot about counter-terrorism stuff, and I think Sam, maybe you were talking about cybersecurity. But anyway, they were both presenting or speaking at this event and they ended up chatting. I think it was, the mutual connection was that Chet, your brother was an intern at SpaceX and I was actively working at SpaceX. My dad was like, “You going to meet my son?” Then I think we hung out at a barbecue or something first.

Ben Grynol: Were you in LA at this time, Sam? Or was that just you went out there for this presentation?

Sam Corcos: I was living in the cloud. But-

Ben Grynol: Why did I ask that question? It’s a silly question to ask you.

Sam Corcos: But I was occasionally in LA. I spent three hours talking with Tim and Karen, Josh’s parents. At some point, Tim just said, “You really need to meet my son Josh next time you’re in LA.” So we did. I think we met at a pool at somebody’s house. Now we’re friends.

Josh Clemente: That’s right. We just grilled out back at a house in, it was in Burbank I think. Then hung out for a while and just kind of talked about … I think we were talking about the spooling up of the Trump campaign. I think that’s –

Sam Corcos: Yeah?

Josh Clemente: I recall spending a lot of time talking about social issues and political developments. At this time, in 2014, it was like, I want to say there were murmurings that Trump was … Maybe that was the second time. Anyway, all I remember is that we jumped straight into kind of deep social and corporate and political conversations almost immediately. That was really fun. That’s the stuff I enjoy. I think we kind of probably spent four hours just in conversation the first time we hung out.

Sam Corcos: Yeah, that’s right. Josh and I stayed in touch pretty consistently after that. Josh had started working a project that was related to glucose monitoring. Which at the time I think it was very much thought of as a hardware project. A lot of those covered in other podcasts how that all happened. But when I caught up with Josh on the phone in May of 2019, I basically said, “Just come up to New York. We’ll spend a weekend just white boarding this idea out and see if it has legs.” I was in the middle of a year off work, just thinking about what I wanted to spend my time on. It seemed like a plausible project. Josh came up to New York. I called in some favors to some venture capitalist friends of mine. Josh had never pitched before. It’s good to get reps in because I had pitched many times. The first pitch didn’t go super well, but then we went back and took that feedback, really changed the concept quite a lot.

Sam Corcos: Then the next several pitches … I think the very next pitch was the health drink from the juice cart that we sell.

Josh Clemente: Yeah, I think so.

Ben Grynol: Okay. When you suggested that Josh had come out to New York, was it circling in the back of your mind, like, “Hey, this is something that I could see myself being involved in long-term.” Or was it more like, “I really like Josh and we’re friends. I wouldn’t mind helping him get more traction with this thing …” just we’ll call it, “as a favor.” What were you thinking about in that respect?

Sam Corcos: Yeah. At the time, it was definitely the latter. I want nothing to do with hardware manufacturing, especially in medical devices. I think my advice to Josh is that building Class III medical devices in a largely commoditized space against highly entrenched incumbents with a lot of IP problems, any one of those is a red flag for why you should not start this company and you have maybe five of them. At the time, it was very much just thinking through some of these ideas and not really thinking about it as something that I would want to do.

Josh Clemente: To fill in some gaps there … Actually, and I do want to rewind all the way to August, 2018 when we ran into each other while I was moving out to Philly. But in the first conversation that Sam and I had, at that point, I had been working on getting the basics of logistically distributing CGMs legally. That was where most of my thinking was. But I was projecting forward into the future and saying like, “The future is building a consumerized CGM. That’s where I think this has to go.” Sam’s correct input was like, “That sounds like the bad portion of the idea. Do not get into medical device construction right now. That’s not going to work out in your favor.” Which definitely there was agreement there. But I think where we coalesced was on, we started to just talk about what the technology did for me and what the technology could be without getting into medical device development and manufacturing.

Josh Clemente: That’s where we very quickly converged in our conversation. Sam, I want to loop all the way back though to August, 2018. Do you recall the brief chat we had about when I was wearing the Libre when we met in Albuquerque or wherever that was, somewhere in New Mexico during that retreat?

Sam Corcos: No, not really.

Josh Clemente: Yeah. I recall just, I think you had made up your mind about, you were moving on from CarDash at that point. I think there was an acquisition happening and you knew the time was ripe. I briefly brought it up and showed the Libre off. I think it was pretty obvious that you were preoccupied thinking about the next steps for your career. Anyway, I always think about that conversation. I spent the next six months doing things that I probably wouldn’t have done if we had just cut to the chase in that conversation. But it’s always funny to remember back to.

Sam Corcos: Yeah.

Ben Grynol: Yeah. I mean, it’s interesting because the way that each of you remember the conversation is different. Where it’s this anchoring point for you, Josh, thinking of how things moved forward until May of 2019. For Sam, it was a little bit more passive. But the interesting thing is, you went for two years, maple syrup, Maple Biometric, Frontier Biometric, eventually Levels. I think that is the sequence-

Sam Corcos: Maple syrup was an offshoot. It was a-

Ben Grynol: That was Kate’s name.

Sam Corcos: That was Kate’s offshoot of the maple biometric.

Ben Grynol: But it still counts in sequence.

Sam Corcos: It does.

Ben Grynol: Two years of pounding the pavement pretty hard. You were, we’ll call it basically a solo founder, even though you were working with one of your former colleagues part-time on Frontier. But where it really changed was when Sam and you had started pitching in New York and he had made this decision like, “Hey man, I want to do this. But if we’re going to do it, I’m going to be the CEO and we have to be okay with that.” I think it would be interesting to unpack that because that’s a tough conversation to have as a solo founder and thinking through how you go from being the founder CEO to the founder and an operating generalist, if you want to call it that word. It’s like, you will always be the founder, but just the sense of what you execute on day in and day out changes.

Josh Clemente: Yeah. I mean, from my perspective, I think the most challenging thing for me there … I would love for this conversation to be about the challenges mostly because that’s where all the lessons learned were. But I went into the conversation with Sam and the pitches really having no expectation that this was about a breakout or co-founding conversations or anything like that. This was about pitching the concept I’d been working on. The pace that Sam Corcos likes to work at is very quick, for those of you that haven’t worked with Sam. The conversations, we had basically pitch day in New York, Sam texted me afterward. By the end of the day, we had had I think, I don’t know, four or five pitches. He texted me. The last one went super, super well. They’re interested in investing. Then there was this flurry of activity. By the time I got … I think it was actually Memorial Day weekend. It was this weekend 2019 that this was happening. There was this flurry of activity. I had shared a bunch of documents with Sam.

Josh Clemente: The thinking that I had kind of put together on both how to get accessibility, but then also where other ancillary markers of health could be tapped into and all of these different concepts. Sam was in the documents. He started distributing them. He started sharing them with people, getting feedback, getting others who can vet this concept involved. That was surprise number one for me. Going from a person who was kind of working on this basically on my own with very few people very interested, to having a ton of people in the documents and Sam himself generating thought at lightning speed was an adjustment. Then by the end of the weekend, he was like, “You should come back up to New York and we should talk again.” I booked another trip and I think it was the week right after Memorial Day weekend. He just went straight into the conversation. Exactly what you said, “I want to be part of this, but I think I should be CEO.”

Josh Clemente: If you can just imagine the two years of very, very slow painstaking ramp up to that moment, and then in the span of less than a week, including a holiday weekend, having this conversation, it was rapid. It was kind of a shock, and I wasn’t expecting it. That’s the biggest thing, is that I was not anticipating that response. I was definitely taken aback and frankly, there’s a lot involved there. You’re trying to play out all the scenarios. there’s ego, unfortunately. Those are the things that I had to very quickly sort of get control of in order to have an accurate conversation to be able to discuss specifically the challenges the company faced and how they should be approached as a team. I think that I’d like to hear Sam’s side of it, but the pace that that conversation developed was tough for me. I think primarily because I was not expecting that, and I had no hint that Sam wanted to be involved really up until that point.

Sam Corcos: For me, it was an interesting situation of stars aligning. Where during my time off, I talked to a lot of other people working in healthcare technology and learning about physician networks and some of the changes in telemedicine laws and how that might apply to this use case. Also using it myself for the first time and realizing how certainly a lot of the dietary habits were the things that were contributing to a lot of the lifestyle issues I was having. When I realized that the real value add here is in the software layer, and my background is in software, it just became increasingly clear to me that, of the various projects that I was working on, that this one had the most potential. When I was talking to Josh about it, it was mostly in the context of the CEO role. I remember Josh wanted to be the CEO and I asked kind of open-ended question of, “Well, how much do you like spending your time taking investor pitches and doing email?” He said, “Well, I don’t really like doing those things.” It’s like, “Well, unfortunately that’s pretty much what a CEO does.”

Sam Corcos: It’s just not a lot of deliverables. It’s a lot of selling. It’s a lot of emailing. It’s a lot of networking and talking to people. Also broadly speaking, I’ve been in early stage for pretty much my entire career. I have a lot more experience and know where all the bodies are buried in early stage and how to avoid a lot of the same mistakes. Having the scar tissue that I have from the many past early-stage experiences, I think would really help to inform the way that we build things going forward. That was the mindset that I had. Which is, there wasn’t really ego attached with the definition of the title. But in terms of what the responsibilities are of a CEO in an early stage company, it felt like the background that I had would be a better fit for it.

Josh Clemente: Yeah. The ability to just have that direct conversation … Basically the first time that we discussed working together was this conversation that we’re talking about. In retrospect, the directness was really helpful because we could talk about the specifics of the role as opposed to slowly kind of dancing around titles and just legacy titles. Because I had been doing this solo, it just makes sense for me to be CEO. It was, let’s go directly to what our going forward, once we form this partnership, what are the responsibilities sets and what fits best? That was very helpful for me because I don’t think we came to terms in that conversation. I think it was probably a day or so later. I was able to just dwell on the past year, two years and the challenges going from that point forward projecting out where I wanted to focus inside the company if I did have not just one other person, but many others. Where would I fit best based on my skill sets.

Josh Clemente: I think Sam’s input there was really helpful because, he’s absolutely right, at the end of the day, the CEO is not the one you picture in your mind when you think about starting a company. You think about all of the sort of glamorous sides of things, where you’re developing new technology and you’re sort of building something and it’s all quite abstract. But in reality, it’s an information router position, and Sam is better than most at not only that, but knowing how to, I think, not just route information, but then as he’ll talk about, the eigenvector centrality. His networking theory is well beyond most people. I just did not have that model for network development, and it just would not have been the right fit. That’s ultimately what helped me out, is just being realistic about, let’s suspend disbelief for a minute and say, this is going to work. Where will I be most valuable? It was obvious to me that it would be supporting that role and not being in that role.

Ben Grynol: It’s funny because Sam’s looking at it from a functional standpoint. Naturally, any person who is a founder would look at it from an emotional standpoint, especially when a conversation is unexpected and delivered synchronously. Sam could be called operations manager. It was more about the function and the scope of work that needed to be done and where he was like, “I know how to do this and add value to take us to the next level.” From an optics perspective externally, having nothing to do with ego, this title or this scope of work is called the puppet master. I am the puppeteer and I have all these strings and I have to pull the strings. Because that is what a CEO is. Is somebody who is a puppet master that knows how to pull the strings and utilize resources. That’s it. If you don’t know how to utilize every resource, if you’ve got a toolbox and you know how to only use one thing, the hammer, all the other tools become obsolete.

Ben Grynol: But if you’ve got enough of a generalist knowledge where you’re like, “I’m not the best at using the saw, but I know what that saw is used for and I know when to use it and how to use it and to make sure that it’s always utilized.” That’s the mindset of a “CEO”. What makes it difficult though when it comes to the conversation is, there are these binary approaches. One was asynchronous. Sam could have texted or emailed you, and you could have sat on that information for a second and processed it. What gets difficult is when information is delivered synchronously to a person that they are not expecting, and it has an emotional sentiment to it, if you want to call it that. You’re sitting there and it’s like, in your mind, you’re trying to do all the mental calculations of like, “Does this mean I’m bad at this job? Where have I gone wrong? What does this mean for the future?” I think that’s natural.

Ben Grynol: But it’s interesting how the two of you were able to overcome this as a hurdle and go, “Wow. If we can talk about this in a rational and a transparent manner, it’s going to actually make our relationship stronger moving forward.”

Josh Clemente: No doubt about it, there was a lot of emotion wrapped up there for me. I think I have a fairly effective radar for my emotional state when in a conversation. I do my best to collect my thoughts and think rationally when having difficult conversations, as opposed to letting emotion override it. But like you said, it’s a timing thing as well if you’re not expecting it. Sam was as direct as we said here. That was, I think the first sentence after we sat down in the conversation is, “I want to do this with you, but I think I should be CEO.” I didn’t expect that at all. Ultimately, the question that Sam asked, which is what I left that conversation thinking about was, “Well, I don’t really don’t care about the title, but I just don’t think you’re going to enjoy being CEO because this is the set of responsibilities that I’ve seen in early stage a CEO needs to take charge on.” That’s what was helpful for me was, this is not a land grab.

Josh Clemente: This is just me trying to let you know that if we’re going to work together, we have to figure this out before, not after things get tricky. We should not be focusing on the title specifically, we should be focusing on the responsibility set. That was helpful. Once I was able to leave the room, spend some time walking and thinking and just projecting out, at this point, success was not really an option in my mind. It was like, I had felt like things were, as you know, tapering off. This was a step change in the other direction. I was feeling optimistic, concerned, my ego was bruised, but also supported. It was a whole bunch of stuff happening at one moment. I think I was able to, with some conversations with my parents and some friends, pretty quickly converge on what I felt was the right move. Which I’m glad to say it was the one we made.

Ben Grynol: Yeah. If Sam had … Let’s throw title aside. Let’s just talk about scope of work. Sam comes in and you both agree. It’s like, “Cool. You’re going to oversee everything to do with engineering.” Because he’s an engineer, he’s got great startup experience and he can move the needle there. Both of you don’t surface this conversation about actual work where you can each add the most value. A month goes by, two months goes by. Resentment can build up because if one person’s expectation is, let’s say the CEO is highly communicative and getting meetings and taking pitches and being an information router, and that work is falling with you, Josh, and Sam sitting there and he’s coding. He’s like, “Man, I know how we should be doing this better, but it sort of just keeps being sort of brushed under the rug.” Eventually you have to surface that conversation of like, “I think we’d be more effective together if …”

Ben Grynol: Like it’s Lennon and McCartney. It’s like, “We can both sing songs and we can both write them, but how are we going to be the most effective? Who’s playing what instruments?” It’s an interesting thing to think about.

Josh Clemente: The nice thing about how the working relationship has developed, I would say that the biggest thing is determining intent or doing your best to interpret the intent of the other person. At the end of the day, you can kind of look at somebody’s principles, how they’ve sort of done things in the past and then try to figure out what their purpose for taking a specific action or saying a specific thing might be. It’s kind of like steelmanning the argument. I think I try and do this often, where it can be challenging to understand someone’s motives. But you can take the summary of your information about that person and make a best guess. It’s best to give that person the benefit of the doubt. I think it could be easy to drive off the rails and say like, “This is Sam just trying to take credit and he’s trying to take over and be captain of the ship.” Or whatever. That you can go in 1,000 different emotional directions. But there’s really no reason at the end of the day for Sam to leave all the opportunity cost he has on the table to take on this project, which has up until that point, been largely stagnant and take the role of responsibility, which many people see externally for that project.

Josh Clemente: Unless he genuinely believes that he can add the value necessary or a couple with the individual who’s already working on it to get to success. It’s that intent. That’s carried through to many other conversations. We’ve, in the past two years, had many challenging points. I think intent and trust are key. It’s hard to have trust without interpreting intent. Trying to assign the best intent to an individual that you know instead of letting sort of emotion undermine and so fear and doubt.

Sam Corcos: Yeah. It’s something that I’ve learned myself having been co-founder in the past, is that these types of, as Ben used the term resentment, resentments can really build in co-founder relationships just as much as they can in interpersonal relationships. Being able to recognize them in yourself and to be able to talk about them and surface them when there are tense conversations and maybe you don’t really know why, trying to get to the bottom of that. Or just very quickly, if there’s some regular activity that’s causing tension or stress, just surfacing that and having a conversation about it. Like, this was maybe a year ago, I brought up to Josh that we really need to improve communication habits. A lot of times this actually happens with engineers a lot where engineers really don’t like doing email, and I can relate to that. But in my current role, I pretty much only do email. I think I average something like three or four hours of email every day.

Sam Corcos: It’s basically my core competency. When you have these things that are causing friction and tension, it’s really easy to sweep them under the rug. I think in the Radical Candor framework, they call it ruinous empathy. Where you don’t want to hurt somebody’s feelings, so you don’t give them feedback. It can cause issues when you feel like you’re doing them a favor by not hurting their feelings, but really you’re setting them up for failure. It continues to build resentment up in yourself. But it also oftentimes builds up resentment in them. Just being able to have those difficult conversations and be able to do it openly is really important for the long-term success of the company.

Josh Clemente: Yeah. I almost think that it is critically important that we started off the working relationship from that vantage point of probably the most challenging conversation. Maybe we’ve had more challenging conversations since, but certainly one of the most. That I think set the stage for the working relationship that can incorporate that direct communication. There’s no doubt that, in the moment when something’s tough, let’s talk about that communication thing, it’s tricky, especially in an asynchronous environment and remote, to not let your emotions get the better of you. When Sam says we really have to improve communication, I think he gave feedback something along the lines of like, “I’m having a hard time knowing or trusting that things are going to get done if I don’t have communication throughout a project.” For someone like myself, who I work pretty well on my own, I also work well with people in person, and I was adjusting to working with people asynchronously, that’s something I had not actually done before in my career. I didn’t have the framework or the structure built yet to effectively communicate what I was doing and why in an asynchronous environment.

Josh Clemente: In retrospect, of course Sam would feel this way. It makes obvious sense. But I felt frustrated by that immediately. It was like, “I’ve been doing all this work. Basically, I haven’t slept, I haven’t worked out. I’m not treating myself right because I’m doing all this work. Yet Sam’s not recognizing it.” Of course, within a matter of a few hours of reflection, you can realize, well, how is Sam supposed to recognize that if he doesn’t have that communication? Over the past few years, one of the most challenging things for me personally, has been developing a mental model that is something like, communicate more than you want to, and then communicate more. It’s something like that. Where it is always, it feels like too much. I still probably don’t even communicate enough now. I’m always looking for opportunities to just provide little breadcrumbs for people who they don’t have access to my inbox, and so they’re not going to know that these little tidbits unless I share them. That’s something that, again, a challenging conversation, it’s tough to take that direct feedback.

Josh Clemente: Especially when you’re not working side by side with that person every day in an office, where it can be on a coffee chat. It’s something where it’s like, “Hey, do you have time for a call today?” You get the call and it’s that direct feedback. Which it can suck. But I really believe that the point here is, again, assigning intent. Understanding why that person is saying what they’re saying. Is it Sam trying to micromanage, or is it Sam trying to improve the structure of our working relationship so that we can not only set the standard for how the company should operate, but get to the point where we even have a company to operate?

Ben Grynol: There is a very good reason why uncomfortable conversations are called uncomfortable. They’re hard on both ends, but they’re necessary. If you avoid them and you don’t do it transparently … This is something that’s hard no matter what, in business, in personal relationships. Is being direct, and back to your point, Josh, about intent, being direct and helping to unpack the intent. Because sometimes it’s hard to really articulate things when delivering feedback or having a synchronous conversation when the information is being transformed between the two parties. But it has to do with the intent. Dancing around the conversation, let’s say you have the uncomfortable conversation but you don’t really hit the nail on the head, you just sort of keep hammering around it, that nail doesn’t ever go into the board and you never really address what needs to be addressed.

Ben Grynol: When doing that, and when people can open themselves up on both ends of the conversation and make themselves vulnerable, it’s uncomfortable when having it. But you leave the conversation, maybe not immediately, like one minute later, but maybe an hour or a day or a week, you definitely feel better. Both sides will feel a sense of appreciation maybe for each other, a sense of respect and trust. It helps to build that foundation of trust even deeper because you go, “I know we can face adversity together and come out on the other end of it in a better place.”

Josh Clemente: I would say it’s the fastest route to getting there for sure. For the wrong personality types, I think it might be the fastest route to understanding that you’re not going to be able to come to terms. But I think Sam and I have a very compatible set of principles, and again, the intentions are aligned. What I think was different is the experience set going into this project. I had sort of a different framework for getting work done. Being a hardware engineer and working onsite and not having a consumer early stage startup experience and be in the sort of software development world, was new to me. Sam had been working, I think, continuously remote. He had visibility into the other side of company issues that I wasn’t really thinking about. I was thinking all about the mechanisms of the business, not so much how the business should operate in order to be successful.

Josh Clemente: To his credit, I think Sam has done a tremendous amount helping us, myself and the rest of the company, to focus on the internal problems that can dismantle us. Whereas I would have focused on the external problems, probably to the detriment of the project overall.

Ben Grynol: I don’t want to say the first conversation was facing adversity because that was just a transparent conversation. But when was the first time as a co-founding team … This might’ve been when it was just the two of you working on it or we’ll call it a month later, like late June, early July, 2019, when David came on board and then Andrew, and then Casey. When was the first time that either the two of you, or even the entire team really faced adversity and then had to overcome it and how did you sort of work through it?

Sam Corcos: Yeah. I think that would have been about a year ago. Is that right, Josh? I don’t remember. I remember distinctly a specific conversation where we had our one-on-one for an hour and I felt a lot of tension in the call. I imagine Josh probably felt it too. Then I think I called Josh back immediately afterwards, and said, “I think there’s some tension here. We need to talk about this.” We blocked off basically the whole rest of the day. I think we spent the next six hours on a Google Hangout talking about it.

Josh Clemente: I think that was around July, 2020, something like that. Basically, the way this ramped up is, it kind of started with the communication conversation that we touched on. But we were at a very tough point operationally as a company. We were resource constrained and we were moving from a very, very janky quarter management system to our internal sort of database that had been built out for order management. I think Sam had spent a very frustrating couple of days dealing with customer records and just there was a lot of mess in the logistics.

Sam Corcos: Yeah, I remember that time. Yeah.

Josh Clemente: I had been lead on just maintaining customer interactions and orders and making sure orders were going out the door at the right time. We were using Google Sheets and this HIPAA secure form provider and a CRM that was really tortured into doing things it wasn’t supposed to do to keep things flowing. We had no database. It was bad. The migration over was just brutal. To be honest, we didn’t communicate well on this little mini project. I think Sam had time open up in his calendar and he jumped in. Didn’t have a lot of context for all of the areas where I was applying band-aids to keep the bleeding down, and so he just had a brutal weekend. I think there was frustration going into this conversation where he had just been, I’m sure, struggling to get this stuff figured out. I was out of the loop on what he was working on. We both were quite frustrated because I had the context that he was missing and I could have probably improved the experience for him.

Josh Clemente: But all that to say, it was kind of a charged conversation. We did our one-on-one. It was not great. Then we kind of touched on, I think, a theme of sort of an organizational structure. It was clear that we needed to grow out of this problem. We needed support on the operation side and logistics side, and we were talking about what that potential hire should do. I just remember feeling as though Sam wanted to take all of those responsibilities and put them elsewhere and relieve me of that set of responsibilities. Frankly, I think at the end of all of the sort of digging we had done, maybe one order had not been correct. Had been missed or something. I had felt like I had actually done a pretty amazing job despite all the janky tools I was using. I was feeling I had done well. It felt to me like Sam was very frustrated by that execution. That kind of sucks. However, the way that we left the conversation it was tense. We decided to schedule another call to dig into why.

Josh Clemente: I think that we spent that next six hours talking about organizational structure. Not just the role to come in to manage logistics, but how the company should grow and where the responsibility should stack up. The thing that was challenging for me was, it wasn’t clear where I fit in that structure. This was certainly, I think one of the most vulnerable conversations I had because it really took a lot of effort to continue to assign best intentions to Sam in this conversation. Because again, Sam, he’s able to just talk about specifics and be very direct. But oftentimes there’s a lot of emotional baggage wrapped up in these conversations that is not occasionally accounted for. I just felt pretty dejected and not appreciated in this conversation. Not only that, but talking about the sort of organizational growth, I didn’t see where I fit in. That’s where we spent the most time. It was just, to steelman Sam, he was basically saying like, “You won’t have to worry about this set of problems, so you can work on any of the other problems this company needs to succeed.”

Josh Clemente: To me, to steelman me, I was like, “It’s not clear that there’s anything here for me to do.”

Ben Grynol: You thought your time was done with Levels?

Josh Clemente: Yeah.

Ben Grynol: You were like, “What more can I do?”

Josh Clemente: It felt very much like being pushed into a corner. I don’t know what exactly changed to be honest with you. I mean, we talked it out, I think honestly through that weekend, for like nine hours. But at the end of it all, looking back on that conversation, it was maybe an inflection point for me, where it actually felt quite freeing to … I think at some point, Sam made a comment along the lines of, “If I were in your position, if I was able to just wash my hands off responsibility, hand it off to somebody else and have nothing to do, that’s the ultimate success.” Although I intellectually understand that, the giving away the Legos kind of concept, it was a challenge to my sense of value or self-worth to the organization. It just took a while for that to sink in. I think it did sink in. I came to terms with like, “This is not the best use of my time. There’s someone better for this. I can focus elsewhere.”

Josh Clemente: We talked a lot about PR and podcasts and hiring and all of the other challenges the company was going to face and how I could support those. But I didn’t see it because I was too frustrated. It took me time to just come to grips with it and then decide, “You know what? I’m not going to waste any time here emotionally wrapped up. I’m just going to go try and execute because none of this matters, we just need to win at this set of problems. It doesn’t matter to me what problems I’m working on. I just need to be helping in some way. It doesn’t matter where I fit on some work chart. Those are secondary issues. Today, the company’s default dead and we’re not going to get any closer to default alive having this conversation go on much longer.” It’s kind of how I remember it feeling.

Ben Grynol: It’s funny because in early stage startups, that is the role … We’ll say, for a generalist role, is getting to reinvent yourself over and over and over, that’s the dream role where you’re like, “I’m going to do this until somebody that’s 10 times better at the job I’m doing can come in and do this. Where you build just enough of a foundation and then you get to reinvent yourself. That’s what you’re doing right now. Is, like right now, you’re deeply involved in everything on the research side of it. Where you get it going and then there will be a time where someone else can do that. Sam can’t just dish off the responsibilities of the CEO.

Ben Grynol: He can’t keep reinventing himself where he’s like, “I’m just going to go code for three months and then I’m going to go and be in operations.” He can, but that’s … I mean, that’s sort of what a CEO does, but only when pinch-hitting. Like, “I’m going to step in here to help out where necessary.” It’s a hard thing to do though, because your sense of worth and value of like, “Maybe my time’s done.” You’re like, “I don’t have much more to add.” It’s a jab and it’s hard to digest. But as soon as you wrap your mind around it, you’re like, “I get it. By reinventing myself, I’m actually incredibly valuable to the organization. If I can’t reinvent myself, that’s the problem.”

Sam Corcos: Yeah. It’s taken an adjustment period for me as well. I’ve been a software developer for close to 10 years. As a consequence, I’m used to having deliverables that you ship all the time. I’d like to think I’m pretty good at it, and I ship a lot. Writing code is really fun. Getting in a flow state, just really knocking things out. You have things to show people. In this role as a CEO, I spend most of my time doing email. I made the analogy to Josh that, if the company is a steam engine, I’m basically just lubricant. I don’t have a lot of specific deliverables anymore. We do our weekly team forums where it’s the team all hands where we talk about all the things that were done that week. I think I have had, in the last six months, maybe one thing that was sufficiently specific to make it onto the all hands highlight slide.

Josh Clemente: I was being generous.

Sam Corcos: Yeah, exactly.

Ben Grynol: That was yesterday with the podcast that you did.

Sam Corcos: Yeah. That’s just because my … But a lot of the things that are done, I have some role in routing information that made it possible. It’s just been a lot of letting go of that and just being comfortable with the fact that I don’t really have very many deliverables. It’s definitely an adjustment period for me as well.

Josh Clemente: I think that might be the biggest for me as well. Is just that, when you’re in sort of an executive role or leadership role at an early stage company, you have all these ideas that like, you’re going to be the one that produces the product. Just becoming more and more comfortable being whatever you need to be so that the team can achieve success. It’s always too abstract until you’re in that moment and then you have to revert back to that mindset. I think many of us on the team have faced this repeatedly. Where you get to an inflection point or you actually pass an inflection point where it’s already too late. You should have already moved past that set of responsibilities and you’re being held back because you’re still holding onto them. It feels like you’ve been doing the right thing all along. You feel very much like, “I’m the one that has to carry this burden. This is the thing that I do extremely well.”

Josh Clemente: It hurts to be told that you need to let go of those things. But at the end of the day, you will experience, I think a tremendous sense of relief and exhilaration in what you actually need to do for the company once you can come to terms and effectively hand that responsibility set off and you see that acceleration happen and you experience it. Once you’ve done that process two or three times, it starts to sink in. But it’s painful and it’s uncomfortable, and frankly, it’s scary to have to be in that moment. I’ve seen this a couple of times inside of our team, and it will continue to happen. This is just, these are the growing pains that the company goes through and the individuals within the company go through as well.

Sam Corcos: It’s an interesting thing that, I advise a number of other early stage companies, mostly informally. A lot of my friends are early stage founders. One of the common things that I see as a source of problems, where the founders are uncomfortable bringing people on the team who are better than them at certain things. When you’re the founder of the company, that’s really your only job. Is to build the team and bring on people who are better than you at doing those tasks. I remember talking with Josh after he interviewed Miz, who now runs operations for us. Where Josh had created this whole structure around interviewing them. He had the technical challenges, he had the answer key. He got Miz’s answers back and they were better than the answer key. He said, “Okay, I guess this is just the new answer key.” It’s just something you have to get comfortable with. Is, you have to have that self-confidence.

Josh Clemente: Yeah. You have to take pride in it. I mean, it should be a source of pride to see how much better the team gets as it grows past you. All of the things that you were doing that barely kept the company going or you the individual, and then looking at where you are after a few key hires, it should be a source of pride and satisfaction. I think, like at SpaceX, it was a directive. If you’re hiring someone, they have to be better than you at the job that you’re hiring for. Otherwise you’re by default diluting the quality of the team. It’s a no exceptions policy and I think that it’s an imperative for a company. You cannot allow ego to get wrapped up there in the hiring process. You’ll suffer in many directions.

Ben Grynol: That’s the Amazon outlook exactly too. What do they call it? The bar raiser for talent. I think one of the hardest things for just people in general to wrap their minds around is, whether in a startup or whether in a corporate world, there’s this outlook that if you’re doing multiple things, like you bounce around … Let’s say that Sam is the puppet master and Sam is pulling strings on resources and saying, “We need utilization over here.” It’s natural for a person to think like, “I’m being taken out of what I’m doing now and being put into this other thing because I’m not doing a good job in the thing that I’m currently doing.” But the puppet master is going, “I trust you immensely. Go get this thing going because we have a gap here.” Understanding the dichotomy of thought between the two parties, sometimes it’s easier to just have the conversation and be like, “You are going over to this area to do this thing because I trust you immensely.” That’s always very, very difficult. I think that, that … I mean, we can unpack it in so many different ways, but there can be a sense of insecurity for people or a sense of like, “Am I valuable? Am I trusted? Am I doing a good job?”

Ben Grynol: That, as soon as you remove that, you have these transparent conversations about like, “This is how we’re going to be better as a company. We need this thing now so that we can bring somebody who’s 10 times better at it to come do it eventually.” It’s a hard thing to do, but it always comes back to trust.

Josh Clemente: Yeah. Not too much to add there? I think trust is tricky. It’s easy to say you got to be able to trust your co-founders, but actually getting to the point where there is mutual trust across the group is, it’s really rewarding and it’s not something that is self-sustaining. It is an active process.

Ben Grynol: Okay. Right now we’re in May. Gosh, it is May. May 29th, 2021. It would be interesting to think about where things are at now. How things are going from a relationship standpoint, from a company standpoint where they’ve evolved to now and then where they’re heading. Even as a co-founding team, we are always going to face these growing pains collectively as a team. That’s natural. It’s always good to reflect on it though.

Sam Corcos: Yeah. I think the relationship between Josh and I is probably at a tie point. Somebody was telling me recently, what they look for in a life partner is somebody where conflict brings them closer together rather than further apart. I think that’s something to look for, where if you can have difficult conversations and you can push past the insecurities and the ego, and you can really understand the motives of the other person, it helps a lot to build a deeper relationship where you can talk about things that are stressful. One of the issues and why founders often talk to their advisors rather than the other founders about challenges they’re facing is that they’re afraid that their insecurities will be seen as red flags and that they might get fired. This was something that some of the companies that I advise the founders have this issue, where they don’t feel comfortable talking to their co-founders about their own insecurities and their own challenges. Being able to surface that.

Sam Corcos: It’s like, what are the things that are causing you anxiety? That’s a question that we ask the founding team every week to better understand where these challenges are so we can address them and move forward from there. I think as Josh touched on and Ben as well, it comes down to trust. You have to trust that your teammates want what is best for you and what’s best for the company.

Josh Clemente: Well, I think that the point about adversity or challenge strengthening the relationship, that definitely is the way I feel. I think that humans kind of develop through experience, specific experiences, acute experiences, as opposed to sort of linearly. It’s almost like, it’s a bad analogy, but people would describe life-changing experiences as things like car accidents or losing a loved one, or almost losing a loved one. Things like this that they sort of shock you into taking a new perspective and zooming out and thinking big picture. There are small examples of that throughout life. I think in building a company, there’s a bunch of those going on. If you can try to focus that, what can sometimes be negative energy into learning how to get better, then I think you become extremely resilient. I would say the key is just, again, assigning best intent to the other party. This person who has decided to basically reformulate their life alongside you for this shared goal, it should be easy to assign best intent to them.

Josh Clemente: But then it’s always going to be challenging to maintain good faith interactions. When you’re in the most challenging conversations, I don’t think Sam and I have ever … Although we’ve had very tense conversations, I can’t think of an example where we’ve used bad faith tactics on each other. Trying to show the cracks in someone else’s character or assigning bad moral principle to one or the other. I can’t think of any examples of setting one or the other up for failure. I think that’s key. Is, despite the complexity and maybe even the scariness of the subject matter, staying principled and supporting each other, and trying to understand the other’s position and then work through it has been uniform. I think that’s the thing that I appreciate most about this working relationship, is that I can trust Sam to bring good faith tactics to the conversation. I certainly do my best to do the same thing for him. I think that’s, despite this not having been effortless or without its challenges, why we are in the best working position today that we’ve been in since starting the company.

Ben Grynol: Yeah. Those conversations, I always think of approaching them from a stance of pragmatism. It’s like you’re pragmatic. It doesn’t mean that you remove empathy or emotion at all, where like you’re just a stonewall to talk to. It’s that you’re pragmatic in understanding what needs to be done, the necessary things that need to be done. But when having conversations, it’s done out of respect. That’s just a principle, that it’s transparency and respect. You’ll never try to … As you mentioned, Josh, it’s not about picking apart character flaws and pinpointing things. “You do this.” It’s more a matter of like, “I’m bringing this up because we have a shared interest and a shared goal together and then as this greater team to get this thing done.” This thing being, we’re building a company. Here are where I see opportunities. Here’s where I see gaps in maybe the way we’re working or the way the things we’re doing as a company. When you try to approach it from that standpoint … You can extrapolate this to personal relationships too, which is a different conversation.

Ben Grynol: But when you use that lens of pragmatism and respect, eventually you can get to the goal that needs to be achieved in having that conversation. It’s always hard to do. One of the questions that I started thinking about though, Sam, when you brought up that you ask people every week, “Hey, what’s giving you a sense of anxiety? What do you have concerns around?” The question is, what do you do when you’re unsure whether or not somebody is answering that question with absolute honesty?

Sam Corcos: I mean, you hope that they do. Sometimes you can pick up on these things with tone. At that point, I think it’s one of the Colson Brothers, asks people specific questions. They put a lot of effort into trying to extract this information. I think one of the questions they ask is, what is something that you really want to tell me, but you feel too uncomfortable to tell me? Trying different tactics to pull that information out. Otherwise I think sometimes it’s through getting other people who are in a different position in the company, somebody where they feel like more of a peer. Because sometimes this is something that I’ve had to adapt to, that people often take what I say much more seriously than it’s intended because of my title on paper. I was talking to Haney, our editorial director, there, he said it was kind of disorienting getting emails from the CEO asking him to look into something. Historically, he feels like he needs to drop everything and this is now top priority.

Sam Corcos: But for me, it’s more like, “Hey, this is an interesting thing. I thought it was interesting. Do it or not, it’s up to you.” Everything that I send is really low priority by default. Just being able to have people on the team who can talk to people who are peers to try to surface some of these things, because it’s possible that I will not be able to just because I have a position of authority that can cause tension in some of these relationships. I think if you’re picking up on things, trying to do what you can to get to the bottom of it. Because almost always, once you surface what the underlying problem is, it is resolvable. That’s the way that I approach it.

Josh Clemente: Yeah. It’s tricky to do that effectively without being accusatory. I think that’s the most challenging part of digging under the sort of the surface. Is making sure that the person understands you’re not trying to accuse them of wrongdoing or hiding things. It’s just that you’re trying to get to that equal playing field where you’re actually discussing the root of the challenge as opposed to dancing around it.

Ben Grynol: Yeah. We’re all imperfect, emotional, irrational human beings. That is what the brain is. We’re not these computers that work on ones and zeros. The hardest part is, on the delivering side of things and on the receiving side of things, when it comes down to communication. Because every person receives and digest information differently. Sam can be told something directly and he just says like, “Cool, thanks for telling me.” It’s just so pragmatic. Other people, let’s say in a personal relationship, you want to tell your sibling or your parents something, it might be received with more emotion. How you deliver that information is much different. That is a very, very difficult thing to do. It’s just, you have to be this chameleon to always adapt your communication style and take the amount of time necessary to work through things. Some people, to receive information, it might take one person 45 minutes to digest that and feel like they’ve got some sense of resolve out of the conversation. Someone else, it might take 45 seconds where it’s like, “Cool, let’s get back to work.”

Ben Grynol: There’s no right or wrong answer. It’s just a matter of adapting, which gets harder and harder because the number of nodes in the network as the company grows increases communication exponentially. That’s something that evolves. Where we’re at right now, May of 21, where are things headed as far as relationships go, dynamics go, team evolution? Where are things headed in that respect?

Sam Corcos: Yeah. Actually one other thing to touch on on the last topic is that, oftentimes people don’t know that they feel a certain way or they don’t have the vocabulary to express it. I look back on my time at CarDash and my co-founder Yinon and I, we have breakfast together regularly. We would talk openly about things or at least we thought we would. I know only in retrospect how I was harboring resentments that I was not surfacing. It’s not like I was hiding them or I wasn’t being truthful, I just was not able to recognize them in myself. I didn’t have the vocabulary that was needed to be able to have those conversations. I think for a lot of it, it’s also helping people learn how to communicate their emotional state at a given time. For some people it sounds like a soft thing to do that is not part of the core mission of the company. But interpersonal dynamics are … I think Y Combinator has a statistic that the majority of companies that fail out of Y Combinator are from bad co-founder dynamics.

Sam Corcos: If it seems like it’s something that’s soft and unimportant, you’re probably wrong.

Josh Clemente: Yeah. I mean, to just take a quick detour, society in general, I believe the discourse is kind of broken for the same reasons that a company can fail. In that people, they don’t work hard to understand … If you simmer a challenging conversation down to its core, it’s rare that two people disagree in principle on what would be best for an outcome. It’s just in the execution where the disagreement happens. But today in society, there’s so much finger pointing and the goal is to expose how the other person is acting in bad faith or beliefs something that is objectively untrue or negative. I think right now we’re trying to, and one of the things I appreciate so much about the team we’re building is that, we’re pushing back on that and working to build a culture where it’s always about meeting each other face-to-face, assigning best intent, and working to understand the misalignment and resolve it.

Josh Clemente: It’s tough in society in general, and it’s even tougher when you then add the pressure of a company building. To your question, in 2021, what we’re focusing on or where we’ll be going, I think I would say we’re going to do more this year than we’ve been able to do in the past two years to recursively improve this environment and continue to lean into these culture areas. The documentation of culture effort that we’re doing just generally speaking, demonstrating through our own example, how trust, intentions, and open communication, what it looks like. Those are the areas. I almost think more about this than oftentimes the real challenges the company’s facing to sort of getting our product launched. It’s like, this is an existential issue of importance for our company, to make sure that we can replicate the improvement through challenge mechanism that Sam and I talked about, but for the whole company. How do we make sure that we’re hiring for people who understand believe and implement these types of things?

Josh Clemente: How do we make sure that the culture at large of the company continues to find areas for opportunity for openness and trust to make their way in. I don’t think we have the whole playbook, but it’s an area that we’re actively spending resources on. I think as Sam just said, you’re wrong if you think that it’s not important or that it’s a waste of resources.

Ben Grynol: Whoever is fidgeting with a Dentyne the gum packet.

Josh Clemente: I think that’s a … Is that like Magic Keyboard?

Sam Corcos: It is … I’m actually was trying to figure out what it is. It’s like a Rubik’s cube but it’s made out of metal. I don’t know. I’m trying to figure out what it is.