Amy Buechler and Michael Seibel on Founder Coaching and Having Hard Conversations

Alright guys, welcome to the podcast. Thanks Frank, how's it going? Great! Good! Amy, you are a founder coach. I think a lot of people don't know what coaching actually is, so maybe you could explain it?

Yeah, that's actually a great question because what coaching is depends a lot on who the coach is, what their expertise is, and what their experience has been. So, coaching in its most simple term is a supportive relationship. It's a supportive relationship that helps people, usually founders or execs like managers, resolve problems that they're experiencing in their life.

So, I think some people might be familiar with therapy and maybe have even done it before. How would you differentiate it from coaching?

Therapy is a relationship that uses that relationship to affect change. Whereas coaching is using the coach's own life experience to affect change. They're both really similar; coaches often use their relationship with the client as information to help them understand the client in order to better serve their needs. But therapy is almost all that. It's all about the client—the client's relationships, the client's marriage, friendships, family—all that stuff. Whereas coaching is the client and their work and their eating habits and this, that, or the other. That's not all the relationship.

Another big difference, actually, is the credentialing process. So, in therapy, for example, I had to go to grad school, I had to get a master's degree, and then have 3,000 supervised hours before even being able to apply to take the licensing exam. So that's five years of my life. Whereas with coaching, one day I decided I'm gonna be a coach, okay? And that's really the difference. You can imagine the different types of people, for example, that would opt into one career path versus the other.

Okay, and so we've kind of outlined a few of the most common problems startups have here. I think what could be most helpful to people is we're just gonna talk about the problems, and then we can outline the symptoms, talk about a couple examples, and just go from there.

Okay, so what is the most common problem you see startups having?

The most common problem I think that I see my clients having is an inability to have difficult conversations because their emotions get in the way, and/or an inability to even pinpoint the actual problem that they're experiencing.

Okay. Often, the real problem is like many levels below what they're experiencing as they go about their day. And so we've broken a few of those out. So we've called them roles and responsibilities, discussing equity, talking about founder performance, and the last one is talking about runway—how much you got left in the bank. So maybe, I mean maybe even Michael, you could give an example of one of these from any of the things you've worked on.

Sure! Yeah, so in the early days of justin.tv and Twitch, roles and responsibilities was something that we did a very bad job at. One of the kind of very clear ways that I know we did a bad job is that every single one of us started another company and did a better job. And so we realized that we fixed it.

Very specifically, we had four co-founders. We were equal co-founders, and while we each sort of knew what we were supposed to do, it wasn't extremely explicit who was responsible for what. It wasn't extremely explicit who was responsible for product. It was extremely explicit for who was responsible for... well actually, you know now that I think about it, it wasn't extremely explicit who was responsible for product.

Hmm. And like maybe that was actually the core issue because it was explicit who was responsible for the hardware—that was Kyle. It was explicit who was doing the software—that was Emmett. It was Justin's show, so there was a transport for filming. And you know, I think I was supposed to be responsible for fundraising and customer support and press, and so forth. But who was responsible for product was actually unclear, and I know that because we fought about it all the time and we changed our minds all the time.

So this is interesting. So this is kind of only one degree of separation, right? So you were just like bickering about product in particular?

Yeah, yeah. And it came across in these absurd ways. Justin and I had a three-day debate about the background color of the website. Justin wanted black and I wanted woodgrain. Our solution, instead of actually deciding who should lead product, was to allow the user to select different backgrounds.

Yeah, and that's exactly what a coach would help with because they have laser vision. They can see past all the layers of criticism and argue and stuff, and they would quickly—I would guess within an hour—probably have been able to see that that was the actual problem. Which would have saved you how much time?

I mean, we didn't figure it out for six years! And you didn't even figure out until like this one moment that it was just product. But this is tricky though too because so many things in startups and in life are gray areas. And so you may not have actually known maybe black would be better, maybe wood grain would be better. The most important things didn't matter, right? Like it wasn't a top three most important thing for our business.

So like when you're arguing about something that's not a top three thing, there's probably—there's a problem, right? And would you say that you were able to argue about that because you didn't have a clear goal in mind?

I think it was because I cared, weirdly. You know, I was the non-technical founder, and there were few things to care about in the early days pre-launch. And like this was something that I could think about. I couldn't think about how to build our first chat system or our first video camera, but I could think about this.

And like what we should have decided is that, no, Justin's going to think about this, and Michael, you're gonna think about these other things. And what's interesting when I think back is in areas where the responsibility was extremely clear, we actually did a good job, right? Kyle’s responsible for the camera, he bought the camera. Emmett built the website. Justin had to show it. I actually did do tons of customer support; I actually organized all this press. I she knows all these sponsorships.

And in those areas where there was no debate about responsibility like we excelled. We did better than expected. And in areas where there was to be strangely, like we got to the right solution. And the screwy thing is we didn't even debate the most important part of things, right? The most important product thing about Justin TV, which is videos on the left and chats on the right—day one videos on the left, chats on the right!

Like we need—we weren't even debating that. We were like debating stupid other things. Oh, people call this bike shedding, right? Choosing what color paint the bike shed, yes? Like that's the big debate rather than building it.

So, so Amy, if you were Michael's coach in this situation, how would you go about walking through like putting a stake in the ground and saying like, "Hey, I'm Michael, I'm gonna run products." Or maybe not?

Yeah, yeah. That's sort of something that's on my mind as I'm listening to you and I'm thinking through a couple of sessions I've had this week where you were a team of four founders. You each had your kind of your own world, although of course they overlapped because it was early days, but you also had your own skill sets as individuals and humans. Yes, hopefully those aligned with your responsibilities.

However, I'm just kind of like imagining you back in the day, Michael. You owned what, like external partnerships?

Yeah, it was basically business stuff, yes. And you had, I think, probably the personality to match up very well and they had never built product before ever. Interesting!

Yeah, but back in that day, like your skillset and stuff maybe wasn't needed as much, right? And so like there's almost this rotating set of gears and wheels where you had all this capacity, you had the bandwidth to worry about everything. And so instead of being able to recognize that in the moment and put your skills to use immediately, right?

Because you're not really needed until all the hardware and everything like gets into place where you can sell it or whatever. Like I forget your question, Craig, but as your coach I would have been able to recognize that and been like what is the most impactful thing that you with your skill set and your particular piece of the pie can like how can you impact the bottom line right now too, knowing that right now, what you want to do isn't important?

And that's fine, and that's good. Like not all cylinders need to be firing at all moments. It's funny that I think that I certainly didn't realize that in the first go-around. And I remember in Socialcam, my second startup, there were moments where I literally was like the most important thing I can do is be here but not talk, like but shut the up! Because it's like we had decided what we're building this week. Everyone knows they were supposed to do, yeah, and like the only thing I could do in a conversation with other people was either waste their time or change the plan, yeah, just shut up!

And like I ended up, I kind of realized this is just TV, but I ended up printing out this thing was like good leadership doesn't require being disruptive. And it was like something I always kept in the back of my mind. It's like I don't need to disrupt—like at some way you just need to sit there and build something. And having someone in your ear is not really helpful for that.

And I'm curious, how did you realize that?

You know, strangely in the second company, our authority roles were different, right? So in the first company, our authority roles were so weird. It was like Justin and Emmet had done a start-up before but they weren't really business savvy, and like Kyle was extremely technical, but he was doing this like hardware thing that none of us had expertise in.

And so it was all—there was this weirdness. Right, I'm with Socialcam even though we all had equal equity the second time, like I had been the CEO before and they were my—they'd been employees. And so I think each of us were more—there was already kind of a natural hierarchy and I think that it was easier for me to give things up because I didn't feel like I was giving up power or authority; I felt like I was delegating.

Whereas like in the early days, it was almost like there were four CEOs.

It does kind of sound like it was a free-for-all, yeah.

For like teams, 'cause I know this is also a common thing where you did have equal equity, you know, you did have equal-ish sounding pie pieces.

Yeah! If in a perfect world, who would have the decision to make the decision and delegate or tell you, Michael, like stay in your lane or whatever?

You know, I think it's interesting, right? I think the story of just abuse, which is kind of—it's funny because Justin started as CEO. And so I think there was probably a time in the early days where you would argue it was his responsibility. I'm post-launch, we need to start fundraising. We switched—I did this extremely poorly—but we switched and I became CEO, and I carried us through for the next kind of five years.

And then when we decided to focus in on gaming, that was kind of Emmett's expertise in his interests, so then he became the CEO. And so it's like crazier as like that—it's really kind of three embedded CEOs, right? And then Kyle goes and starts Cruise and needs to see it!

So I'd like—so I think that at various times it was various people's responsibilities. I think by the time we came to Emmet, we were just older. We had seen dysfunctions like, man, if you see dysfunction for long enough and you're reasonably smart, you're gonna be like okay, I think this function's not good, we should fix that.

But in the early days, we were just like we don't know; we never worked in companies, we don't know what good looks like, right? Ego at the time, yeah.

Well, three out of four people were in it to Yale, so that also...

Hey, I wouldn't advise that!

You mentioned equity. Equity is another interesting one. So, Amy, how does that come out? And what are the symptoms of maybe an uneven or just like a perceived uneven equity split?

How could...

This is an interesting one. In my experience, the way it comes out is the person who feels as if they have less equity than they deserve is usually the one who calls me. They call me usually at the point at which this conversation has boiled over such that they feel so much resentment towards the person who has more than they deserve or whatever that they don't know anymore if they can even continue on.

That's how it comes up in my experience. As you can imagine, you know when you feel resentment, that causes so many other downstream effects; like you can't—you no longer respect the person, you're short with them, everything they do irritates you. It sort of like pervades you every part of your waking and sleeping life. You have jury and I and me like deeply want to malign them.

And the solution there is just to like have a sort of a come-to-Jesus moment with yourself and ask yourself like should we renegotiate this? Is it worth it? Can I salvage this relationship with this person? Be open to it, or—and/or is there a price at which I will let, you know, can I present a different deal at which point I might walk?

Like am I comfortable walking? And/or an exploration of the past reasons why it was okay for this person to even find themselves in the situation at hand. And that actually to me is the more interesting—like that exploration is more interesting to me as a coach. Usually, the person from the very beginning felt as if something wasn't quite right, like when stuff went to and didn't say it.

Yeah, yeah! And didn't say anything! And it's like—so like why did you? It's like silence yourself. What was it about you that didn't allow that—like you to negotiate for your own self? What was it about you that disallowed you from seeing your own value? And those are patterns that often not only affect the relationship with the co-founder but many, many other relationships in that person's life.

So, it's funny because you talked—we talked to the opposite person. So you talk to the person who feels like they didn't get enough. I talked to the CEO who’s usually in the role of distributing. And this was an area where Justin was amazing from day one—a kind of set up precedent. I remember that you know in Justin TV when he and Emmet asked me to join up and I was like “Hey, I will, but I want to feel like an equal partner.” And he was like “Great! You're an equal partner!”

And I remember being like “Oh!” You know, I remember like that moment—I felt like I am all in! Yeah, right? And we were doing an online reality TV show, there was no reasonable reason to be all in, but I was like “Well, if I’m an equal partner, I’m always, you know.”

And it was interesting because when Kyle started, he had only 10% equity because he had started as like a quasi employee, quasi contractor kind of thing. And we were trying to like convince him to join up. And there was a point, I think three or four months in where Kyle was like “I’d like to be an equal co-founder.” And I remember thinking to myself, “Okay, what's my model for whether you should be?” And it was like, “Well, Justin established it.”

So, Amber, thinking like immediately, my first reaction was not “You negotiated this, you should stick to what you negotiated.” I didn't—I did it. My first reaction was like, “Well, what do Emmet and Justin think? Are they cool, right?” You know it was very much like open to that conversation.

I think a lot of times when I talk to CEOs now, you know the reason why I like to default to equal is it kind of just gets rid of this conversation, right? But this is not a best fit for all circumstances.

But it's hard to see: now the number one thing that they say to me is, “Well, we negotiated it!” And it's like so funny because I'm like, “Look, as a CEO, you're thinking about your co-founders' motivation today but also five years from now.” And they might not be thinking about that and so it’s not a fair negotiation.

Like, like victory is not you negotiated a deal for themselves; victory is they work really hard the whole time! Like you can't let them negotiate a deal for themselves that's not gonna make them work really hard.

And so it’s so funny. I have to tell me like “Hey, look, this isn't some business transaction; this is, you know—when you're coming to get sold, the company acquires you, basically puts this massive retention, you know, if you do well, puts a big retention bonus that sits out there. It's called golden handcuffs, and it’s to keep you there.

Yeah, and I often tell CEOs equity is golden handcuffs. Equity is what keeps people there, it's not a reward! It's like—it's a—it’s a bondage in a weird way. And so like, do you really want this person to be around? Well, if you don't, then why are they your co-founder? If you do, you should probably give them a lot.

It's so interesting that you say that, too, because often, again, it's so funny. I'm talking to the opposite person, like the person who feels as if they're being devalued. And it's interesting because I always find I have to tell them how their behavior must be perceived by the CEO because this person has been sitting on this thing for years sometimes.

And it's like coming out in all these random passive-aggressive critical wave kinematics is like, “We already decided on this way!” The CEO often doesn't even know where it's coming from at all, and they're like “Why is this person being crazy and unreasonable and like horrible to me? And why have they been for years?”

Like they just sort of are often blindsided because in their mind it's been negotiated.

Yeah, and it's so interesting that that again, like the people that I'm talking to, they're so filled with resentment they can't possibly imagine what's in that other person's mind. Yes, and so like again, it just, it pervades their experience.

Um, there's something else to say, but I forgot it.

Well, it's weird to say that I think that in situations where the equity should be unequal, like it's honestly situations where the people with lesser equity are comfortable with that for a long period of time.

Like that is a situation, right? Where you know sometimes you have companies where different founders bring many different things to the table; and so you know, one founder, you know with Justin TV is like four founders who are basically done nothing, right?

Like it didn't feel like equal at—like equal equity felt like it made sense, right? In a situation where like there's a massive power imbalance and someone is bringing like a lot more to the table than someone else, right?

Like you can kind of make a case, but the new—the reason why you know there's agreement on that is because the person doesn't blow, like the person with less equity doesn't get pissed two years from now.

Yeah. And like if that wasn't correctly done, yeah.

Yeah, so so, let's say you are in a situation where you might be getting less equity. Do you have like a good model for playing that out in your head? Like in five years, am I okay with that? And like maybe that's just a simple exercise you can do because you're basically like ideally you would just avoid this entirely, this conversation.

Right? Five years down the line, I think ideally it requires either the founder needs to step up, right? Like the CEO needs to step up and be honest and be like “Hey, look, I want to make sure regardless of what you think you need now, let's talk about what you think is going to make you feel great five or ten years from now.

Let's talk about like, let's imagine we sold this company and I make more money than—like let's really talk about that! Is that gonna feel comfortable? Is it gonna feel comfortable for me to get ten times the money than you, or two times more, and have done it?

Alright, habit or I think on the flip side for that, you know, co-founders, it's not the CEO to just be like very explicit about “Hey, these are some of the reasons why I believe you should have more equity. And these are some of the reasons why I believe I should have more.”

I feel like it requires one person to step up and I see a lot of situations where neither step up.

That's absolutely true! The person with the least amount of equity will never be okay with it, you know? So, I am always like this is always going to be a problem until something changes, and so you might as well bite the bullet and change it one way or another and just like—and just have the conversation.

The other interesting thing that I'm thinking about as we're talking about this is again, the reason why some folks sort of enter into this negotiation and then are fine with it—I mean fine— (air quotes) yeah, say they're fine with the equity split, even when they're not. Is because they have such a difficult time speaking to their value and saying I am worth this because I'm amazing and I have all the experience that you need.

I also will just say that like women often have a harder time being able to do that. And so I just want to make sure that that again from a coaching perspective, that that conversation like “I don't feel as if I have value” erupts, not just in the equity conversation, but in many other instances too, especially for example with first-time managers, especially for example with managers who are managing really amazing, like the C-suite, and they're great—like they don't feel as if they're valid enough to coach the other person, say “I’m holding you accountable. You didn’t meet my expectations in this way.”

So again, that piece of “I don't know if I have enough,” if I can't see my value, you know that shows up in so many different ways in my work.

My mind, if you're the CEO on this one, I think the buck stops with you. Like I think that either person could step up, but I think the CEO's responsibility is to stop them.

That's very big of you!

I think that's the plan! If this is a problem like this, it's the CEO—this is kind of core! So, so many of these things really just boiled down to communication, right?

Like simpler, more transparent communication.

Yes, of your intentions and your feelings, yes! Is there a point where there's too much?

Yeah! Like yes, from a founder—from a CEO's perspective, maybe if your CEO is like in a funk one day, maybe I shouldn't be communicating today, right? I don't know, what do you think?

I mean, my first reaction was like yes, of course! Too much of anything is not good. Everything needs to be in balance.

I think in general though, people hesitate to communicate about feelings and about difficult topics. And in that world, it's never a bad idea to over-communicate because it you can—like imagine it as exercise. You need to build muscles, you need to communicate and deliver feedback to everybody in a different way, based off of how they receive it, their own life experiences, and how they're feeling that day.

And so especially when you're first starting out, like over-communicate the feedback, over-communicate the difficult messages, give each other feedback on how the feedback is going, you know?

Like but develop like healthy amount of hygiene there, but like, yeah, when you're—when you're arguing, when the communication isn't productive, and when it's not even coming from a good place, too much of that is certainly not good.

Well, I think you just made an amazing point. In general, I don't encounter companies that are over-communicating!

That's very—absolutely! But I do encounter situations—and I'm thinking back to my personal experience—where it's a non-productive communication.

Uh-huh!

Yeah, where it's like we’re having a fight; we know we’re having a fight, it’s not gonna solve anything—just stop fighting!

Yeah, just don’t let it go! Don’t keep on having the fight!

And I definitely feel like when I was younger, I've somehow thought there was value in winning the fight and I didn't realize that like maybe every minute after 20 minutes where you're fighting, you're just reducing the value of your company!

Like you're just hurting everything!

Okay? So it’s just like you can't—not fight at all, but it's just like there is a diminishing return for your core goals!

Yeah, I know one team who has a limit of every time they notice they're fighting, they set a timer for two minutes. And then they literally stop the conversation and like take a walk around the block and don't revisit it until the next day!

And I hated that because I always had—I always worked things out through talking!

Like I couldn't work things out only in my head; I had to kind of have a competitive seeing it in competitive South River! But it is—and I wouldn't catch feelings about it!

Yeah, like I like fighting, but arguing I like arguing, but it's not productive!

And many times, like, if the other person isn't on that same wavelength, you're not helping!

Yeah!

Yeah, that’s kind of what I was thinking. It's good and totally fine that like you need to talk things through. And the more different opinions that come at you, the better the output—like the better the final idea. But if I'm coming from a culture or a family in which like strong opinions terrify me and I feel overwhelmed because any conflict makes me feel a sweat—like I'm sweaty just thinking about, you Michael, in your style for example!

Like that won't work for me. And again, like your style isn't bad, and my style isn't bad. They both have pros and cons. And again, it's just a matter of like knowing that and being able to talk about it and being like—and yeah having conversations about it so you can find a middle ground that works for everybody!

Yeah, and it's hard too. It's funny that it's—if I were smarter back in the day, I think I would have created no consequence arguing time.

Like I would have separated out thinking through things out loud from decision making! And so I—and so it never would have felt like those thinking through out loud moments had much consequence!

Yeah, right? Because like when I'm just working through my stuff, like it shouldn't be a consequential conversation! Like I might change my mind!

Like, you know, like I'm the kind of person who’s like—I strongly, strongly felt but very loosely held opinions, right?

So I think later on I kind of learned how to just like separate decision making from conversation.

And I think knowing you, Michael, the one thing that you always do really well is you—in the whatever argumentative conversations—not just in your style—you always are only talking about the idea!

And so many founding teams, especially when they get into patterns of like bad communication hygiene, are talking about the other person!

Okay, I'm gonna pause you right now because I know what you're saying isn't being helpful—but I know what you're trying to say! What you’re trying to say is that person beat like co-founder. When you’re when you do this with this product, my impact of the product is that or whatever—yeah, like redirect the conversation to the actual task or not the person!

Like that.

Yes! Because there are certain situations we arguing because what you're really saying is like you're not doing your job, right?

I've had one of those conversations recently, and I know it was painful for the other person, and I know I just didn't have the balls to say I don't think you're doing your job. So I had this really awkward like where I tried to almost make it so that they would come to that conclusion themselves, which is really stupid, it's really dangerous!

Well, but that's the next thing we wanted to talk about. So that's a performance, right?

Yeah! There you go!

Yeah, so symptoms of feeling that someone's underperforming?

Yes! I have been thinking about this actually, so I have come to the conclusion that in my clients who have performance issues of one kind or another, there’s actually usually two types of performance problems.

One is a real performance problem where their co-founder actually isn't meeting goals and not like meeting the deadlines, maybe not showing up to work as frequently—like just sort of like they’re bowing out? That is a real problem.

And so that's one bucket. And then the other bucket are perceived problems of performance where, again, like same thing, like one person doesn't think that the person is meeting expectation, you know?

And like, but it's all imagined! And in the first category—the real performance problems, like that is solved with having a conversation. Be like, “Hey, like I noticed that you're not meeting actual expectations; you know what's up with that?”

That almost always actually is about burnout; it's not about the person's performance, it's about their losing motivation.

When it's a perceived problem, that is when things get a little bit trickier because that means that goals haven't been decided, often roles and responsibilities aren't clear, there hasn’t been agreement that the expectations and goals are even worth pursuing.

Usually, like so again, so performance is a really wide category of issues in my mind. They're one of two: real or perceived roles and responsibilities.

So often at the core of this like so often like if it's not roles and responsibilities, someone should be fired because it's like in an early-stage startup like if someone can't actually do the work, right?

Right, it’s kind of like you kind of need—I do though to get the work done, but it’s so rare that someone can't do the work right!

Like it's extremely rare!

So many founders interact with this—not they can't do the work, it’s like we don't know what we're doing! What's the goal? Did we write it down?

Totally!

Whose job is it to do this, in what timeline? Yeah, we never really wrote—like oh, like you want to pull this feature? Did you write a spec?

No! Do you even agree what the feature should—you know, right? So it's like, well, how would you expect someone to go the magical thing in your head?

You know? Totally right! And so so much of that’s roles and responsibilities. And the other thing that I think about with performance that I think is extremely important for CEOs is like your job is to manage motivation.

Like I think a lot of times people talk about like 10X engineers and like it's almost as if there's this idea that like people's DNA is different, and that's the only important factor in their output.

And like I would argue that even more important than their DNA and like how raw smart they are is how motivated they are.

And like often times people don't talk about like you can't change the DNA but you certainly can change the motivation. And like what I've seen, you know, even here in YC is that like it's amazing what work people will do when they feel good about the workplace, and it's like—it’s just like it’s that simple!

Like they’ll blow you away! They’ll do things that you didn't even expect them to do, they'll do things even more impressive than you could have hoped for if you set up an environment where like people want to buy in and if you set up a buy more they don't like—I don't even do the simple things!

And so like I've seen far more 10X difference based on motivation than I have based on like DNA.

And I've worked with some amazing engineers; don't get me wrong, and like they're magical! But man, like you put a magical person and they’re highly motivated, they're easy!

I think you bring up another interesting topic which is how especially early-stage CEOs mostly can keep their team motivated even during the trough of sorrow because in my mind, it is a skill!

Like there are very few founders who come out of the womb with that charisma and the vision setting and the power, you know, it is really hard! And do you have any—I don't know—I guess I wasn't good at it!

I mean, it's interesting advising companies on it because I just am brutally honest. Like, I just I'm like it’s gonna suck!

Yeah!

Like I don't want to—it's not rosy! Like the fact that we even named the trough of sorrows at YC is like just trying to be brutally honest.

It's like half of not feeling bad is expecting it!

Yeah!

And like we've started telling people, you know: “Oh, when you—when it's not working, it sucks.” And then I've started—they're like—and when it's working, it sucks too because like I just don't—like I just hate having the conversation with the founders.

Like, it's taking off and I just, I feel like every day I'm getting punched in the face! I'm like, “Oh, that's—that’s sorrow! We didn’t tell you that, but yeah, that’s also—yeah, you'll always feel punched in the face!”

Yeah, and Dalton says something interesting, which I've kind of adopted as well, which is that like you have to enjoy the work, right?

Because the emotions are always gonna be that! It’s always gonna be hard to know better! Like what you're doing, because if you're succeeding, you feel like crap! If you're failing, you feel like crap!

So like you're not gonna stick with it if you don't enjoy what you're doing or at least the people you're working with!

I've noticed there has to be like some time—it doesn’t have to be that you love the product, it doesn't mean you love the customers.

There has to be something inherent that's not like “we're gonna make a lot of money!” It's—most people! Right?

Something inherent in the work that you like, even if that thing changes.

Like, this week I love the team, this week I feel more aligned with the product, and that's what's getting me out of bed!

You never change, but it's got to be something anchors it!

It has to be... some work regardless of whether you succeed!

Yeah!

Well, I think it just spirals because if you don't like—if you can't add a little levity to these conversations, you're gonna suffer!

Yeah, it's like constant—alright, last one is runway.

Yes! So what are the symptoms of not having enough money or feeling like you don't have enough money left?

That's an interesting question! For some reason, where my—so this one I like as a coach, I don't get a lot of folks whose runway is less than four or five months because coaching is effing expensive!

You know? And so like right out of the bat, it’s unfortunate actually. It's a problem in therapy too where the people who have the most need are those who can't afford the solution.

And I have not yet been able to solve that problem somewhere in my career. I hope I will!

Um—but weirdly where my brain went was in fact the founders whose companies nearly died. Like were one to two months away from dying, and they like white-knuckled their company out from the grave in order to like live for another year or two!

And yet still live every day with that like fear baked into every cell of their being!

So, and so it’s sort of like runway for me, the clients that I see and then I speak with most are those who are so tired of living in fear.

And yet whose like systems have not yet awakened to the idea that they can have a different life and choose not like make options not from that stance of fear, but rather from the stance of “Oh, I can do this! I can now! Now I have the runway, now I have the growth, now I have the team, the world is bright and shiny again.”

But for some reason, I don't believe it yet.

Yeah, you're the runway problems I see are a little different! I never—I, yeah, it’s weird!

I would probably see three problems. I see the problem that's most society correlated with runway is: It's going to die and I feel bad, and I feel like I've let down my employees and investors.

And we kind of have a hard conversation with the founder, we're like, “Look, your job was to try not to succeed! No one in this setup thought this was 100%!

Yeah!

The other problem that I see is founders who don't realize that runway is a problem, right? That's extremely common.

Like we have six months left, but everything's great! Like we, you know, we've got twenty-five people, we don’t have product market fit! Burning all the money in the world!

But everything's great! And you're just like, “Dude, are you—did you really...?”

Yeah!

And then the other kind of folks I see—I see more of are the people who got their company out of the grave!

Those folks—and that was just a TV experience!

Like those folks I'm more see them being really good—like I'm more see them being like, “Well, if we can get through this, we can do anything!”

And like to me those are the folks who are exciting! It's like those the folks where they're now fearless! They now finally feel in control.

I think as a founder you often feel like investors control your fate! Can I raise this round or not?

The second that you get your company profitable, you for—I think it's for the first time you feel like a business owner!

Like my decisions affected the success of my company as opposed to like only a day if I don’t convince this dude with a bunch of money we don't succeed.

And like to me that was amazing!

I actually don't think we clearly and strategically thought about our business for six years because we were constantly changing fundraising.

You know, the second we got profitable, we were like—it was like a clear-minded like okay what’s the opportunity here.

And it’s not a coincidence that like Socialcam and Twitch both happened after we got broke even!

Yeah, like before that, it was just... (music)

Yeah, that's where I see that! Like there's so many things I'm thinking about what you just said. One of them is yes, like the founders who can dig their company back from the grave, like absolutely!

The best and are awesome in in my work! Then there also becomes a question of can't—do I still have the energy given given what it took me to save my company? Can I still keep going?

Yeah, right? So like there's a real sort of question of is this possible still given everything that's changed for me in the last couple of years?

Oh yeah! And we felt that too!

Mm-hmm!

We definitely felt that too!

Mm-hmm!

Yeah!

How did you solve for it?

I don't think we did! I mean, it's not a—it's...

I don't think we did! I mean you just got major factors in us in me deciding to sell Socialcam was like it's been eight years of struggle!

Like someone's give me some money!

Like yeah, yeah! And they were definitely point suggested to be before we had product market fit before we figured out which that whole thing where we got profitable!

Like we were gonna sell to IAC, we were gonna sell to Google!

Like we—I think we were just like, “Hey, can we get a win on the board?”

And it sucks because man, I talked to founders now who say that, and like my friends—thinking back like I always tell them it's like those wins aren't important!

What are you talking about, right? But like when you're in the trenches, any win feels better!

Right? Anyone give me five bucks and call it an acquisition, I'll take it rather than getting punched in the face every day!

And so I probably should be a little bit more, you know, sensitive to that feel!

Yeah, I think that's interesting that something I was floated through my mind this whole time was how easy it is to see from the outside like, “Oh, of course! Like, yeah, your life is horrible, but it can all be solved because you have roles and responsibilities and need to be clarified!”

You know?

Like it's so easy from an outside perspective to know what is going on and to pattern match and to be like this is where you know, you should head and all this stuff.

And when you're in the moment when everything is on fire and nothing is working, it's so hard to step outside of it and look through like through a different...

But that's just wisdom broadly, right? It's the same thing as like scarcity mindset, abundance mindset!

Like only when you're 35 years old and have some cash can you be like, “Dude, when I was 18 man I could have done anything!”

When you're 50 you say, “Man, when I was 35 man, I could...”

Shameless plug only because it's organic and natural here—that's exactly why coaching is helpful!

Yeah, it's because there's someone who knows you almost better than you know yourself and can ideally pattern match based off of their own experiences and everything they've observed and be able to tell you in the moment so you don't have to look back, but you know, 20 years later!

It's funny because you know when you and I started talking about coaching and this object in general, I was against it completely! I was just like—I was just like what you do as a founder: you suck it up!

Like Son, your job is to suck up the pain, right?

Like Michael Jordan doesn't complain when he has to shoot a thousand shots every day; he does his job, right?

And what's interesting is I think that I've realized what I actually meant.

I think I didn't realize the power and kind of the insight that PG and Jessica had was putting companies into batches!

Because in reality, my coaches were my batch mates and the other people in YC!

And like in reality when I needed outside perspective, I wanted support—that was my like support system!

And like even to today, right? Like those are my friends!

But like, you know, Steve from Y Combinator or I'm in from Twitter!

I just, right? Like I can go to these people and at various different times they've had various different experiences, level of experience, right?

They’ve been ahead of me, behind me!

And so that kind of built this group of people that I could have kind of coaching conversations with and they’re friends!

So they know you over time, right?

It's—it’s funny that I'm only realizing it now.

So I basically was like, “Oh yeah, that coaching is because I kind of have five coaches!”

And I do think most founders—anymost founders don't do that!

I see most founders don't have a lot of friends who do startups, like most founders don't have people they know who are further along than them, indebted or not!

And so like in a weird way, there are some situations where like you just don't have access to that!

I think that's true! And I think also many founders—so I see only the YC founders in my practice, and even they have that community. They have you guys as partners to rely on!

But they often don't have the language to even talk about like what they're experiencing!

And they like there's just sort of like—so again sort of coaching as a supportive relationship, but it's also you learning to have a relationship with yourself!

So in your own mind, you can get clear about how I'm feeling and what my goal is for today and what my schedule looks like and how do I treat myself today! And that’s so like there’s a foundational level of the work too that’s important!

I think we were amiss before we—and to not talk about like what are some of the tools to have these conversations!

Because I feel as though once you're in this chain you should have them, there's still an advantage to like having a game plan!

Yeah, you're really good at giving people that game time!

Thank you Michael!

Yeah! Like in terms of say there’s a conversation—responsibilities conversation, right? You met three people, you know?

Yeah! How do we do it? How do we make it productive?

Yeah, we've talked about this a little bit in this podcast, like one is a certain amount of removal and objectivity!

Like take a step outside of your life for a hot moment and be like this is what the company needs!

Like what are the roles that are needed? What are the tasks that each role needs to be done? What are ideally for this company and where we're at how much money we have—this is what one might do!

And then you sort of like plug yourself in!

So essentially, it's like you—you build a map based off of what's needed in the moment.

And in terms of actually having the conversation, stick to the task! Talk about the task! Don't talk about your co-founder and what his breath smells like and how he totally failed at you know last week and how much you hate him!

But you talk about again the task, the project, the idea—all that stuff!

And then also speak only as much as possible, only from your own experience!

So use I statements—say, “I think, I value, I believe, I've noticed,” and your own feelings if necessary!

And do not assume anything from your co-founders!

Like ask them questions like, “What do you think? What is your observation? Or what is your experience, Ben’s considering you've done this for you know five months or whatever?”

How do you approach it when you think that maybe part of this conversation is removing a responsibility from someone or defining the responsibilities in a way that you know someone's gonna be angry about?

Mm-hmm, yeah.

So how to have that really tough conversation?

And I'm thinking like as the CEO? Like CEO needs to happen!

I would—in my experience, the CEO initiates this conversation?

Yeah! It’s cool! Really sure?

Yeah, totally!

I mean this is what I would suggest—like Craig, I'm removing the podcast from your job description! Great!

I would like be really thoughtful about how you might take that knowing that you're probably gonna have feelings!

So I'd think about everything that I know about Craig and what your life is like. I would like be quite explicit in terms of setting up the meeting!

So I would like, you know, say, “Craig, I'd like to talk to you about this and this,” like and like literally put it on your calendar, that is different than me just catching you in the middle of our workspace!

Anything! I definitely have clients who have done stuff like that!

Got a second?

Being explicit and intentional about having this conversation and then doing a little bit of prep.

And like sitting down and literally even writing on a script for myself if necessary where it's like, “Craig, I know you've been blah blah blah something-something podcast podcast, and unfortunately like we're going in a different direction and so I need you more here.”

Or, you know, like, “I’d redirect your energy toward this,” but then also explicitly say, starting at this date, we're no longer gonna have the podcast.

And so like again, I would—I would not say I’m taking this away from you.

I’d say I’ve been thinking, and I think your energy is best suited in this direction!

And be specific again, like put projects or whatever on your plate!

And then I would be explicit and say, as of DATE, which I would set in advance, podcast is dead!

But say that in much nicer words!

So then really that structure is a little bit more CEO to employee.

Yeah! How does it change when its co-founder to co-founder?

And maybe, you know, there's CEO to co-founder relationships that are hierarchical, yeah? And then there’s kinds that are kind of like—we see a lot—I'd say it's kind of... not?

Right? It looks like you have owners and someone as a CEO title, yeah?

Like that—I don't really know, you tell me!

Like in my mind, I don't know if I’d give very different advice!

And I’ll tell you—I’ll tell you what!

Like I'm assuming it's a—we're co-founders?

Okay, the in my mind the conversation is quite similar!

But I would assume that there's a level of trust and goodwill between us that's foundational such that if I were to have a difficult conversation and say, “You know, my opinion is that we should move away from the podcast in order to do something else,” you would not take offense and you would want to ask me some questions to clarify.

And then again, assuming trust and goodwill, like you would be okay with this experiment assuming that it—you know it’s just an experiment!

But it doesn't regret our lease job!

A great point!

That's why the department in you, do how do you know in that situation where it's like I think—like I’ve had those conversations where the person has kind of gotten it, right?

Like you kind of make the case, and the person you know sometimes like having the conversation is me, I like thinking about the conversations where people then have it, definitely!

Other side is like, “Yeah, the podcast hasn't been going well!”

Like well they’ve been avoiding it, too!

Yeah, exactly!

But there are other situations where like Craig would say, “Well, no, the podcast has ten thousand listeners every week! Like this is important part of our brand, this part of our strategy!”

Mm-hmm!

Like, you know, there are other situations where it's actually more of a question!

So yeah, like my response to that is ideally you would already have roles and responsibilities outlined.

You know which I would think that would solve whatever this hypothetical question is where like Craig would get to decide what the social—like what we're doing socially!

And like would have probably cleared that in advance, you know?

We're all in alignment because it’s directly linked to whatever our company goals.

Yeah! It's a really good point!

Yeah! To me, it kind of sounds like it’s possible the metric changed!

Yeah! Or if you didn't have a metric in the beginning, then you messed up exactly!

Right?

But if it was neither in then, interest a matter of taste then it gets really tricky!

Yeah!

To me like if you've assigned roles and responsibilities, you shouldn’t—right?

Like if the role responsibility is like Craig is figuring out the social media strategy!

Then like, like either you trust him to do it, yeah?

And then it’s his test that runs the show!

Yep!

Or you don't and you're moving the role you're removing responsibility!

That’s exactly right!

Yeah, because you're—and before you we realize this, you would be micromanaging Craig, and of course Craig wouldn’t take well today!

It's not your place to be doing that anyway!

That's a really good point!

And this is that I actually see that dynamic all of the time!

The other thing I would say in regards is something you said a while back is—say you do whatever remove podcast from Craig’s...

So sorry about your life, Craig!

But you can tell that Craig has like weird crinkly feelings about it but nobody that like he’s not saying anything!

Yeah!

I always asked like how are you feeling?

Like how is it?

I know how much time and effort you spent on the podcast; I know it was like near and dear to your heart!

Like I'm—I don't want to be the bad guy!

But like tell me, you know!

Tell me what's up!

You know, and so you kind of like put your friend and colleague hat back on!

You check in with them personally!

Yeah!

And give them an opportunity to share however they felt about how you were right!

And so that gets all the like creepy crawlies out of the closet and you can like smash them together!

And then you can like walk out of the door, you know, and apologize or whatever!

Take care of the feelings and get back to work!

It's funny because even in this example, we kind of illustrate what happens in a startup where it’s like we almost pre-assumed there weren't roles or responsibilities!

Yeah!

Like the solution was being quite about that upfront!

I feel like that conversation is a more collaborative conversation though—what our roles and responsibilities are is a more collaborative founder conversation!

Right!

And again, ideally, each person's role and responsibility is linked back to that company-wide metric and a goal!

Like—and their skills!

And their skills, exactly!

A much more of a—yeah, like you said before, it's a dispassionate like resource skill matching, absolutely!

Power distribution! Right!

And also knowing that maybe every six to eight months that conversation needs to be re-hashed again just given—especially in the early days, probably before seed is—change!

Things change, yeah!

Totally agree!

No, it's good not to surprise people!

So I think that was the one you wanted to get to, right?

Oh yeah!

So there’s one question from a Jeannie McCallister, right?

Jeannie McCallister asks, “What's the single most important piece of advice you can give a founder?”

My single most important piece of advice that I would give to any founder is to be brave—and that means to start having difficult conversations if they're on your mind!

You know? You know you need to have them!

And that also could mean being brave by getting into therapy and like learning to sit with yourself and the creepy-crawlies of your own mind and your own feelings.

Actually, it takes a lot of courage, and not enough people do it!

Also, Jeannie McCallister is my mom, so thank you mom!

You know mine is one that originally comes from PG and Trevor to the founders of YC where they would call us every week and say “Launch!” And it was funny because I was the single non-technical founder of justin.tv, and I was just like, “I can't! There's— I can't press the button! I don't even know where the button is!

Do you fit?”

And they were just common like, “Why haven't you launched yet?”

And it's so funny because there is so much—you can talk and talk and argue about pre-launch that just like after you’ve launched, it's like a—you’re completely out of order!

And like the longer you spend in that pre-launch, and if you are dysfunctional, the longer you spend in the pre-launch, like the more like it’s a perfect environment for dysfunction to grow!

Yeah!

Whereas like once you're launched and you have conceited customers yelling at you, it's a lot more clarifying like what you should be talking about, what you shouldn't be talking about!

We didn't talk about the background on justin.tv ever again after!

So yeah, like it's in some ways what's so funny is that like you don't have to do any of these things to be successful!

Like a lot of the successful companies we know are in various degrees broken!

Absolutely, yeah!

There's just like these are kind of hints and tricks that help me grease the skids a little, but the reality is like the bigger thing is like did you launch your product?

Do you care about the problem?

Is the product solving the problem for the customer?

And like, I hate this. One of the best quotes on culture I've ever heard, and it's just—it’s sucky from like an intellectual place, but it's really true is that like it’s all easier to have great culture when the product’s working and the company’s succeeding!

Yeah!

Like, you just started instead of starting at Addie and having a wickiup, you're starting to be plus; like this is a lot easier!

Cool!

Alright, well thanks so much guys!

These guys, thanks for having me!