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

by Y Combinator3/27/2019

Amy Buechler is an executive coach for startup founders.

Michael Seibel is a partner and the CEO of YC.

In this episode we talk about coaching and use examples from Michael’s time working on and Socialcam.

You can find Amy at her site and on Twitter at @amybue.

Michael is on Twitter at @mwseibel.


00:10 – What is coaching?

00:40 – How is coaching different from therapy?

2:00 – What are the most common challenges founders in coaching have?

2:55 – Challenges with roles and responsibilities at Twitch

7:15 – How would Amy have coached Michael around roles and responsibilities?

9:10 – Not being disruptive as a leader

11:00 – Switching roles at Twitch

12:15 – Uneven equity splits

14:30 – Distributing and negotiating equity

20:45 – Communicating your own value

22:20 – Can there be too much communication?

23:40 – Productive arguments

27:40 – Talking about performance issues

29:45 – Setting clear goals and managing motivation

32:45 – Enjoying the work

33:30 – Conversations about runway

36:20 – Digging your company out of the grave and continuing

39:50 – Michael being against coaching initially

42:00 – How to have hard conversations

43:45 – Removing a responsibility from someone

49:20 – Returning to roles and responsibilities

50:10 – Jeanie McCallister asks – What’s the single most important piece of advice you can give a founder?


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Craig Cannon [00:00] – Hey, how’s it going? This is Craig Cannon and you’re listening to Y Combinator’s podcast. Today’s episode is with Amy Buechler and Michael Seibel. Amy is an executive coach for startup founders. Michael’s a partner and the CEO of YC. In this episode we talk about coaching and use examples from Michael’s time working on and Socialcam. You can find Amy at her site, and on Twitter @amybue. Michael is on Twitter @mwseibel. All right, here we go. Welcome to the podcast.

Amy Buechler [00:33] – Thanks Craig.

Craig Cannon [00:34] – How’s it going?

Michael Seibel [00:35] – Great.

Amy Buechler [00:36] – Good.

Craig Cannon [00:36] – 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.

Amy Buechler [00:43] – Yeah, that’s actually a great question because what coaching is depends a lot on who the coach is and what their expertise is and what their experience has been. 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.

Craig Cannon [01:08] – Some people might be familiar with therapy and maybe have even done it before. How would you differentiate it from coaching?

Amy Buechler [01:15] – Therapy is a relationship that uses that relationship to effect change. Whereas coaching is using the coach’s own life experience to effect 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. 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 their relationship. Another big difference actually is the credentialing process. 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. That’s five years of my life. Whereas with coaching, one day I decided, I’m going to be a coach. That’s really the difference and you can imagine the different types of people, for example, that would opt into one career path versus the other.

Craig Cannon [02:20] – We’ve outlined a few of the most common problems startups have here. What could be most helpful to people is we’re just going to talk about the problems and then we can outline the symptoms, talk about a couple of examples and just go from there. What is the most common problem you see startups having?

Amy Buechler [02:39] – The most common problem, that I see my clients have is an inability to have difficult conversations because their emotions get in the way. An inability to even pinpoint the actual problem that they’re experiencing. Often the real problem that is many levels below what they’re experiencing as they go about their day.

Craig Cannon [03:05] – We’ve broken a few of those out. We’ve called them roles and responsibilities, discussing equity, talking about founder performance. The last one is talking about runway, how much you have left in the bank. Maybe even Michael, you could give an example of one of these from, any of the things you’ve worked on.

Michael Seibel [03:24] – Sure. In the early days of and Twitch, roles and responsibilities were something that we did a very bad job at. One of the 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. We did a bad job and we realized it and 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 wasn’t extremely explicit for who was responsible for, well, actually, now I think about it. It wasn’t extremely explicit who was responsible for product. Maybe that was actually the core issue. Because it was explicit was responsible for the hardware. That was Kyle. It was actually explicit who was responsible for doing the software, that was Emmett. It was Justin’s show so he was responsible for filming and I think it was exclusive for me that I was responsible for fundraising and customer support and press and so on and so forth. Who was responsible for the product was actually unclear. I know that because we fought about it all the time. We changed our minds all the time.

Craig Cannon [04:44] – This is interesting. This is only one degree of separation, right? You were just bickering about product in particular?

Michael Seibel [04:51] – It came across in these absurd ways. Justin and I had a three day debate about what the background color of the website would be. Justin wanted black and I wanted woodgrain. Our solution instead of actually deciding who should head product, was to allow the user to select different background colors.

Amy Buechler [05:16] – Beautiful. So simple.

Craig Cannon [05:18] – Between black and woodgrain….

Amy Buechler [05:25] – That’s exactly like what a coach would help with because they have laser vision, they can see past all the layers of criticism and arguing 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.

Michael Seibel [05:41] – I mean, we didn’t figure it out for six years.

Amy Buechler [05:44] – And you didn’t even figure out until like this one moment that it was,

Michael Seibel [05:47] – That it’s us and just product.

Amy Buechler [05:48] – There wasn’t a roles and responsibility it was just product. Yeah. Totally.

Craig Cannon [05:52] – 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 woodgrain would be better, right?

Michael Seibel [06:01] – Well the most important thing is it didn’t matter. Well 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, probably there’s a problem.

Craig Cannon [06:14] – Right.

Amy Buechler [06:14] – And would you say that you were able to argue about that because you didn’t have a clear goal in mind?

Michael Seibel [06:21] – I think it was because I cared weirdly. I was the non-technical founder and so there were few things to care about early days pre-launch. This was something that I could think about. Know 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 going to think about these other things. 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 responsibility was the camera. He built the camera, Emmett built the website. Justin had a show. I actually did do tons of customer support. I actually organized all this press. I actually organized all these sponsorships. In those areas where there was no debate about responsibility, we excelled, we did better than expected. Areas where there was debate, strangely like we got to the right solution. The screwy thing is we didn’t even debate the important product things, right? The most important product thing about and Twitch is videos on the left and chats on the right. Day one, videos on the left, chats on the right. Today, videos on the left, chats on the right. I mean we weren’t even debating that. We were like debating stupid other things.

Craig Cannon [07:40] – Well, people call this bikeshedding, right? Like if you’re choosing what color to paint the bike shed.

Michael Seibel [07:44] – Yes.

Craig Cannon [07:45] – It’s like that’s the big debate rather than building it. 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 going to run product or maybe not.

Amy Buechler [07:58] – Or not. 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 skillsets as individuals and humans.

Michael Seibel [08:18] – Yes.

Amy Buechler [08:19] – Hopefully those aligned with what your responsibility is. However, I’m just kind of imagining you back in the day Michael, you owned what? External partnerships? Sales?

Michael Seibel [08:30] – Yeah, it was basically business stuff.

Amy Buechler [08:33] – Business stuff, and you have I think probably the personality to match.

Michael Seibel [08:37] – I do.

Amy Buechler [08:39] – I’m very, yeah, exactly.

Michael Seibel [08:39] – And awkwardly, I’d never built product before ever.

Amy Buechler [08:41] – Interesting. Yeah,

Michael Seibel [08:42] – So I had no skillsets.

Amy Buechler [08:43] – For sure, of course. 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 have the bandwidth to worry about everything. 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 gets into a place where you can sell it or whatever. 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 skillset and your particular piece of the pie can, like how can you impact the bottom line right now today?” 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.

Michael Seibel [09:30] – It’s funny that I think that, I certainly didn’t realize that in the first go around. 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 fuck up. Right, because it’s like we had decided what we we’re building this week. Everyone knew what they were supposed to do. The only thing I could do in a conversation with other people was either waste their time or change the plan. And then so I decided to just shut up. And I ended up, I kind of realized it’s just TV, but I ended up printing out this thing. It was like good leadership doesn’t require being disruptive. 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 point you should just sit there and build something and having someone in your ear is not really helpful for that.

Amy Buechler [10:21] – I’m curious, how did you realize that?

Michael Seibel [10:27] – Strangely in the second company, our authority roles were different, right? In the first company, our authority roles were so weird. It was like Justin and Emmett had done a startup before but they weren’t really businessy. Kyle was extremely technical, but he was doing this hardware thing that none of us had expertise in. There was this weirdness, right? With Socialcam, even though we all had equal equity the second time, I had been the CEO before and they’d been employees. 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 like, it was almost like there were four CEOs more or less.

Amy Buechler [11:19] – It does kind of sound like it was a free for all.

Michael Seibel [11:21] – Yeah.

Amy Buechler [11:22] – Because I know this is also a common thing. Where are you did have equal equity, you did have equal-ish sounding pie pieces. In a perfect world who would have been able to make the decision and delegate or tell you Michael, like stay in your lane or whatever like, don’t just

Michael Seibel [11:40] – Well I think it’s interesting right, I think the story of 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. Post launch, we need to start fundraising, we switch. I did this extremely poorly, but we switched and I became CEO and I carried us through for the next kind of five years. Then when we decide to focus in on gaming, that was kind of Emmett’s expertise and his interest. Just then he became the CEO. It was like crazy, right? It’s like there were kind of three embedded CEOs, right? And then Kyle goes and starts Cruise. Do you guys see what this was like? At various times it was various people’s responsibilities. By the time it came to Emmett, we were just older and we had seen dysfunctions, like man, if you see dysfunction for long enough and you’re reasonably smart, you’re going to be like, “Oh, okay like dysfunction’s not good. We should fix that.” But in the early days we were just like, “We don’t know.” We’d never worked in companies. We don’t know what good looks like.

Craig Cannon [12:39] – Plus a little bit of less ego at the time.

Michael Seibel [12:41] – Well three out of four people went to Yale. I wouldn’t advise that.

Craig Cannon [12:48] – You mentioned equity. Equity is another interesting one. Amy, how does that come out and what are the symptoms of maybe an uneven or just like a perceived uneven equity split?

Amy Buechler [12:57] – Equity 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 any more if they can even continue on. That’s how it comes up in my experience. As you can imagine, when you feel resentment that causes so many other downstream effects. You no longer respect the person, you are short with them. Everything they do irritates you. It’s sort of like pervades you every part of your waking and sleeping life. You have dreams about this person, you know what I mean? Deeply you want to malign them. The solution there is just to like have sort of a come-to-Jesus-moment with yourself and ask yourself 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, but you know, can I present a different deal, at which point I might walk. Am I comfortable walking? And or an exploration of the past reasons why it was okay for this person to even find themselves in that situation at hand. 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 with you too.

Amy Buechler [14:38] – I didn’t say it. Yeah, and didn’t say anything. And it’s like, and so like why, why did you silence yourself? What was it about you that didn’t allow that? You to negotiate for your own self? What was it about you that disallows 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.

Michael Seibel [15:02] – It’s funny because we talk to the opposite person. You talk to the person who feels like they didn’t get enough. I talk to the CEO, who is usually in the role of distributing. This was an area where Justin was amazing from day one and kind of set a precedent. I remember that, on, when he and Emmett 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, okay.”

Amy Buechler [15:35] – Easy.

Michael Seibel [15:36] – And I remember like that moment I felt like I am all in.

Amy Buechler [15:39] – Yeah.

Michael Seibel [15:40] – 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 all in.” It was interesting because when Kyle started, he had only 10% equity because he had started this like kind of 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.” I remember thinking to myself, “Okay, what’s my model for whether you should be?” And he was like, “Well, Justin established it.” I remember thinking immediately my first reaction was not, you negotiated this, you should stick to what you negotiated or did it up. My first reaction was like, “Well, what do Emmett and Justin think?” It’s like, “If they’re cool, I’m cool.” It was very much open to that conversation. A lot of times when I talk to CEOs now, the reason why I like to default to equal is it’s kind of cheats. It kind of just gets rid of this conversation. If this is not a best fit for all circumstances. When I talk to CEOs now, the number one thing that they say to me is, “Well, we negotiated it.” It’s like so funny because I’m like, “Look, as the CEO, you’re thinking about your co-founders’ motivation today, but also five years from now.” They might not be thinking about that. It’s not a fair negotiation. Victory is not, you negotiated at 50. Victory is like, they worked really hard the whole time.

Michael Seibel [17:09] – You can’t let them negotiate a deal for themselves that’s not going to make them work really hard. It’s so funny, I have to keep being like, “Hey look, this isn’t some business transaction.” This is when your company gets sold, the that company acquires you basically puts this massive retention, if you do well, puts a big retention bonus that sits out there and it’s called golden handcuffs and it’s to keep you there. I often tell CEOs, equity is golden handcuffs. Equity is what keeps people there. It’s not a reward. It’s bondage in a weird way. Do you really want this person to be around? Well, if you don’t, then why are they your co-founders? If you do, you should probably give then a lot of equity.

Amy Buechler [17:52] – It’s so interesting that you say that too because often again, it’s so funny, I’m talking to the opposite person, the person that feels as if they’re being devalued. 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. It’s coming out in all these random passive aggressive, critical ways.

Michael Seibel [18:19] – The CEO can’t imagine because it’s like, “We already decided on this, right?”

Amy Buechler [18:21] – The CEO often doesn’t even know where it’s coming from at all. They’re like, “Why is this person being crazy and unreasonable and like horrible to me? And why have they been for years?” They just sort of are often blindsided because in their mind it’s been negotiated. And it’s so interesting 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. Again, it pervades their experience. I had something else to say but I forgot it.

Michael Seibel [18:52] – What’s weird too is that I think that in situations where the equity should be unequal. It’s honestly situations where the people with lesser equity are comfortable with that for a long period of time. That is a situation, where sometimes you have companies where different founders are bringing different things to the table and so, one founder… With it was like four founders who had basically done nothing. Equal equities felt like it made sense. In a situation where there’s a massive power imbalance and someone is bringing like a lot more to the table than someone else, you can kind of make a case but the reason why you know, there’s agreement on that is because the person with less equity doesn’t get pissed two years from now. And if that wasn’t correctly done,

Amy Buechler [19:47] – Then they will, yeah.

Craig Cannon [19:49] – Let’s say you are in a situation where you might be getting less equity. Do you have a good model for playing that out in your head, like, “In five years, am I okay with that?” Maybe that’s just a simple exercise you can do because you’re basically ideally you would just avoid this entirely, this conversation, five years down the line.

Michael Seibel [20:07] – Ideally, it requires either founder needs to step up. 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 was going to make you feel great five or 10 years from now. Let’s talk about like, let’s imagine we sold this company and I make more money than you. Let’s really talk about that. Is that going to feel comfortable? Is it going to feel comfortable for me to get 10 times more money than you? Is it going to make me feel comfortable two times, one and a half…” Or I think on the flip side for that co-founder and 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. By the way there requires one person to step up and I see a lot of situations where neither step up.

Amy Buechler [20:56] – That’s absolutely true. The person with the least amount of equity will never be okay with it. I am always like, this is always going to be a problem until something changes. You might as well bite the bullet and change it one way or another. And just get it over with, 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 this. I mean “fine” in air quotes. 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 am amazing and I have all the experience that you need. I also will just say that women often have a harder time being able to do that. I just want to make sure that that again, from a coaching perspective, that conversation, 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. 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 expectation in this way.” Again, that piece of, “I don’t know if I have enough, I can’t see my value.” That shows up in so many different ways in my work.

Michael Seibel [22:19] – 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 step up.

Amy Buechler [22:28] – That’s very big of you, I love that.

Michael Seibel [22:30] – If this is a problem like it’s the CEO’s because this is kind of core.

Craig Cannon [22:42] – So many of these things really just boil down to communication. Right, like simpler, more transparent communication.

Michael Seibel [22:47] – Yes.

Craig Cannon [22:48] – Of your intentions and your feelings.

Michael Seibel [22:47] – Yes.

Craig Cannon [22:51] – Is there a point where there’s too much?

Amy Buechler [22:53] – Yes.

Craig Cannon [22:53] – From a founder, from a CEO’s perspective, maybe if you’re a CEO who’s like in a funk one day, maybe I shouldn’t be communicating today, right?

Michael Seibel [23:04] – I don’t know. What are you thinking?

Amy Buechler [23:06] – My first reaction was like, “Yes, of course, too much of anything is not good. Everything needs to be in balance.” In general though, people hesitate to communicate about feelings and about difficult topics. In that world it’s never a bad idea to over communicate because you can 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 in that day. And so as, especially when you’re first starting out, over communicate the feedback. Over communicate the difficult messages, give each other feedback on how the feedback is going, but develop a healthy amount of hygiene there. 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.

Michael Seibel [23:54] – Well, I think you just made such an amazing point. In general, I don’t encounter companies that are over communicating. That is very rare.

Amy Buechler [24:02] – Absolutely.

Michael Seibel [24:03] – But I do encounter situations and I’m thinking back, my personal experience with where it’s a nonproductive communication. Where it’s like we’re having a fight. We know we’re having a fight. It’s not going to solve anything. Just stop fighting and just don’t keep on having the fight. I definitely feel like when I was younger, I somehow thought that there was value in winning the fight. I didn’t realize that 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. You cannot fight it all, but it’s just like there is a diminishing return for your core goals.

Amy Buechler [24:42] – 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 take a walk around the block and don’t revisit it until the next day.

Michael Seibel [24:52] – And I hated that. Because I always worked things out through talking. I couldn’t work things out only in my head. I had to kind of have a competitive thing and competitive is not the right word, but it’s kind of good. I wouldn’t catch feelings about it. I like fighting…arguing. I like arguing. But it’s not productive in many… And if the other person isn’t on that same wavelength, you’re not helping.

Amy Buechler [25:27] – That’s kind of what I was thinking. It’s good and totally fine. You need to talk things through. The more different opinions that come at you, the better the output, the better the final idea. If I’m coming from a culture or a family in which strong opinions terrify me and I feel overwhelmed because any conflict makes me feel like I’m sweaty just thinking about you, Michael and 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. Again, it’s just a matter of 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.

Michael Seibel [26:07] – It’s funny that if I were smarter back in the day, I think I would have created no consequence arguing time. I would have separated out thinking through things out loud from decision making. And so it never would have felt like those thinking through out loud moments had much consequence. Because like when I’m just working through my stuff, it shouldn’t be a consequential conversation. I might change my mind. I’m the kind of person that’s like, I strongly felt, but very loosely held opinions. And so, I think later on I kind of learned how to just separate decision making from conversation.

Amy Buechler [26:57] – And I think knowing you Michael, the one thing that you always do really well is you, in the whatever argumentative conversations, just in your style, you always are only talking about the idea. Many founding teams, especially when they get into patterns of bad communication hygiene are talking about the other person. That’s the moment where it’s like, “Okay, I’m going to pause you right now because I know what you’re saying isn’t being helpful, but I know what you’re trying to say.” And what you’re trying to say is that person B, like co-founder when you do this with this product, my impact of the product is that or whatever. Redirect the conversation to the actual task and not the person.

Michael Seibel [27:36] – I really like that. Yes, because there are certain situations where you’re arguing because what you’re really saying is you’re not doing your job.

Amy Buechler [27:40] – Totally.

Michael Seibel [27:41] – 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. 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.

Craig Cannon [28:00] – Just avoidance, man. It’s really dangerous, well, but that’s the next thing we wanted to talk about. That’s performance, right?

Amy Buechler [28:05] – Yeah.

Craig Cannon [28:06] – There you go.

Amy Buechler [28:08] – Amazing.

Craig Cannon [28:09] – Symptoms of feeling that someone’s underperforming.

Amy Buechler [28:14] – Yes. I have been thinking about this actually. 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 meeting the deadline, maybe not showing up to work as frequently, like just sort of they’re bowing out. That is a real problem. That’s one bucket and then the other bucket are perceived problems of performance where again, like same thing, one person doesn’t think that the person is meeting an expectation, but it’s all imagined. In the first category, the real performance problems, that is solved with having a conversation and be like, “Hey, I noticed that you’re not meeting the actual expectation, what’s up with that?” That almost always actually is about burnout. It’s not about the person’s performance, it’s about they’re losing hope,

Michael Seibel [29:16] – Motivation.

Amy Buechler [29:17] – 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. And usually like, so again, so performance, really wide category of issues. In my mind, they’re one of two real or perceived.

Michael Seibel [29:43] – Roles and responsibilities so often are the core of this. If it’s not roles and responsibilities, someone should be fired. Because like in an early stage startup, if someone can’t actually do the work, it’s kind of like you kind of need to get the work done. But it’s so rare that someone can’t do the work. It’s extremely rare. 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?

Amy Buechler [30:20] – Totally.

Michael Seibel [30:20] – Whose job is it to do this? Oh, and we never really talked about this.

Amy Buechler [30:23] – In what timeline exactly?

Michael Seibel [30:25] – Yeah, in what timeline? Are we never leave it like, “Oh like, you want to build this feature? Did you write a Spec?” No. “Do you even agree what the features should do?” No, right. Well how would you expect someone to build the magical thing in your head and you’re not telling them?

Amy Buechler [30:36] – Totally.

Michael Seibel [30:37] – So much of that’s roles and responsibilities. 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. But I think a lot of times people talk about 10x Engineers. It’s almost as if there’s this idea that people’s DNA is different and that’s the only important factor in their output. I would argue that even more important than their DNA and how raw smart they are is how motivated they are. And often times people don’t talk about, you can’t change the DNA, but you certainly can change the motivation. What I’ve seen, even here in YC, is that it’s amazing what work people will do when they feel good about their workplace. It’s just that simple, they’ll blow you away, they’ll do things that you didn’t even expect them to do. They’ll do things that are even more impressive than you could have hoped for if you’ve set up an environment where people work to buy in. If you set up an environment where they don’t, they don’t even do the simple things. I’ve seen far more 10x difference based on motivation than I have based on DNA. I’ve worked with some amazing engineers, don’t get me wrong. They’re magical, but man, you put a magical person and they’re highly motivated, crazy, amazing.

Amy Buechler [31:56] – 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. There’s very few founders who come out of the womb with that charisma and the vision setting and the power, and it is really hard. And do you have any, I dunno, I guess,

Michael Seibel [32:20] – I wasn’t good at it. I mean it’s interesting advising companies on it because I just am brutally honest. I’m just like, it’s going to suck. I don’t want to, it’s not rosy. Like the fact that we even name 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.

Amy Buechler [32:40] – Yeah.

Michael Seibel [32:42] – We’ve started telling people, “Oh, when it’s not working it sucks.” Then I’ve just started being like, “And when it’s working it sucks too” because I just hate having the conversation with the founders like, “It’s taking off and I feel like everyday I’m getting punched in the face.” I’m like, “Oh, that’s sorry. Oh, we didn’t tell you that.” You’ll always feel punched in the face. Dalton says something interesting, which I’ve kind of adopted as well, which is that you have to enjoy the work. Because the emotions are always going to be there. It’s always going to be hard. You better like what you’re doing because if you’re succeeding, you feel like crap. If you’re a family, you feel like crap. You’re not going to 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 some tie. It doesn’t have to be that you love the product, it doesn’t have to be that you love the customers, it has to be something inherent that’s not like, we’re going to make a lot of money. Because most people aren’t going to make any money. Something inherent in the work that you like.

Amy Buechler [33:39] – Even if that thing changes. 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.

Michael Seibel [33:46] – You’ll never change it, but it’s got to be something anchoring you to the work.

Amy Buechler [33:49] – Totally.

Michael Seibel [33:50] – Regardless of whether you’re succeeding or not.

Craig Cannon [33:51] – Yeah, well I think it just spirals you through it. Beause if you don’t if you can’t add a little levity to these conversations, you’re going to suffer. It’s like constant. All right, last one is runway.

Michael Seibel [34:00] – Yes.

Craig Cannon [34:01] – What are the symptoms of not having enough money or feeling like you don’t have enough money left?

Amy Buechler [34:08] – That’s an interesting question. For some reason we’re mum. This one, as a coach, I don’t get a lot of folks whose runway is less than four or five months because coaching is f’ing expensive. And so 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. 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 white-knuckled their company out from the grave in order to live for another year or two and yet still live every day with that fear baked into every cell of their being. It’s sort of like runway for me, the clients that I see and that I speak with most are those who are so tired of living in fear and yet who’s systems have not yet awakened to the idea that they can have a different life and 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.”

Michael Seibel [35:29] – The runway problems I see are a little different. I probably see three problems. I see the problem that’s most side-correlated with runway is it’s going to die and I feel bad and I feel like I’ve let down my employees and my investors and we kind of have to have a hard conversation with the founder and we’re like, look, your job was to try not to succeed. No one in this setup thought this was 100%. The other problem that I see is founders who don’t realize there are runways problem. That’s extremely common. We have six months left, but everything’s great. We’ve got 25 people, we don’t have product- market favor burning all the money in the world, but everything’s great. And you’re just like, dude, are you, did you, is really? It doesn’t sound great. 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 experience, like those folks, I more see them being really good. I more see them being like, “Well if we can get through this, we can do anything.” And to me those are the folks who are exciting because those are 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, I think it’s for the first time, you feel like a business owner, like my decisions affect the success of my company as opposed to, well you’re dead if I don’t convince this dude with a bunch of money, we don’t succeed. I’m like to me that was amazing.

Michael Seibel [37:06] – I actually don’t think we clearly and strategically thought about our business for six years because we were constantly chancing while raising. And the second we got profitable, we were like, it was like clear minded and we’re 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. Like before that it was just… That’s why I see that.

Amy Buechler [37:33] – There’s so many things I’m thinking about what you just said. One of them is yes. The founders who can dig their companies out of the grave, absolutely the best and are awesome in my work. Then there also becomes a question of do I still have the energy? Given what it took me to save my company, can I still keep going? There’s a real sort of question of is this possible? So given everything that’s changed for me in the last couple of years.

Michael Seibel [38:03] – That’s true.

Amy Buechler [38:04] – Yeah, yeah.

Michael Seibel [38:05] – And we felt that too. We definitely felt that too.

Amy Buechler [38:10] – How did you solve for it?

Michael Seibel [38:13] – I don’t think we did. I mean, I don’t think we did.

Amy Buechler [38:20] – You just kept going.

Michael Seibel [38:21] – One of the major factors is in me deciding to sell Socialcam was, it’s been eight years of struggle. Someone’s giving me some money. Yeah, I’ll take that. There were definitely point to before we had product market fit. Before we figured out Twitch and that whole thing. Before we got profitable, we were going to sell to IAC, we were going to sell to Google. I think we were just like, “Hey, can we get a win on the board?” And it sucks because man, I talk to founders now who say that. And thinking back, I always tell them, it’s like those wins aren’t important. What are you talking about? But when you’re in the trenches, any win feels better, right? Any win, give me five bucks and call it an acquisition, I’ll take it. It better than getting punched in the face every day. And so I probably should be a little bit more sensitive to that feeling.

Amy Buechler [39:09] – Yeah, I think that’s interesting. That’s something that’s floated through my mind this whole time was how easy it is to see from the outside. Like, “Oh, of course… Yeah, your life is horrible, but it can all be solved because you have roles and responsibilities that need to be clarified.” 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 should head and all the 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 at it through a different lens.

Craig Cannon [39:43] – But that’s just wisdom broadly. It’s the same thing, it’s like scarcity mindset, abundance mindset. Only when you’re 35 years old and have some cash, can you be like, “Dude, when I was 18 man I could’ve done anything.” Then when you’re 50 you’re just like, “Oh, man, when I was 35 man, I could have done anything.”

Amy Buechler [39:59] – Totally. It’s shameless plug only because it’s organic and natural here. That’s exactly why coaching is helpful, is 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 20 years later.

Michael Seibel [40:19] – It’s funny because when you and I started talking about coaching and this subject in general, I was against it completely. I was just like, you know what it is, right? I was just like, what you do as a founder is you suck it up. 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 goes and does his job, right? 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 with putting companies into batches. Because in reality my coaches were my batch mates and the other people in YC. And in reality when I needed outside perspective or wanted support, that was my support system. And even today, those are my friends, but like, you know, Steve from Reddit or Emmett from Twitch or Justin, 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. They know you over time, right? And it’s funny that I’m only realizing it now, so I basically, was like, “Oh yeah, that coaching is bullshit because I kind of have five coaches right?”

Michael Seibel [41:33] – Yeah, exactly. And I do think most founders, I mean most founders don’t do YC. Most founders don’t have a lot of friends who are doing startups. Most founders don’t have people they know who are further along than them and dah, dah, dah, dah. And so like in a weird way, there are some situations where you just don’t have access to that.

Amy Buechler [41:50] – That’s true. also many founders, so I see only YC founders in my practice and even though 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 what they’re experiencing and there’s just sort of so again, sort of coaching as a supportive relationship, but it’s also you learning to have a relationship with yourself. 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 sort of like there’s a foundational level, of the work too that’s important.

Michael Seibel [42:28] – I think we were amiss before we end to not talk about what are some of the tools to have these conversations. Because I feel as though once you understand you should have them, there’s still an advantage to having a game plan. You’re really good at giving people that game plan.

Amy Buechler [42:45] – Thank you Michael. So you’re saying sort of say there’s a tough conversation that,

Michael Seibel [42:53] – So we need to have a roles and responsibilities

Amy Buechler [42:54] – Yeah, yeah, totally.

Michael Seibel [42:55] – Conversation or a team of three people. How do we do it? How do we make it productive?

Amy Buechler [43:01] – We’ve talked about this a little bit in this podcast. Like one is a certain amount of removal and objectivity. Take a step outside of your life for a hot moment and be like, this is what the company needs. 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 and how much money we have. This is what one might do. And then you sort of plug yourself in. Essentially it’s like 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’d totally failed at last week and how much you hate him.

Craig Cannon [43:43] – Sweaty hands.

Amy Buechler [43:45] – Don’t tell people that they have sweaty hands. 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. 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-founder. Ask them questions like, “What do you think? What is your observation?” Or, “What has your experience been considering you’ve done this for five months or whatever.”

Michael Seibel [44:14] – How do you approach it when you think that maybe part of this conversation is removing the responsibility from someone? Or define their responsibilities in a way that you know someone’s going to be angry about.

Amy Buechler [44:31] – So how to have that really tough conversation. You’re thinking as the CEO, like CEO needs to have a tough conversation.

Michael Seibel [44:37] – I would, in my experience, the CEO initiates this conversation a little bit. Really should.

Amy Buechler [44:46] – Yeah, totally. This is what I would suggest. Like, “Craig, I’m removing the podcast from your job description.” I would be really thoughtful about how you might take that knowing that you’re probably going to have feelings. I’d think about everything that I know about Craig and what your life is like. I would be quite explicit in terms of setting up the meetings. So I would say, “Craig, I’d like to talk to you about this and this.” Literally put it on your calendar. That is different than me just catching you in the middle of our workspace, and saying it for example, which like I definitely have clients who have done stuff like that.

Michael Seibel [45:22] – Hey, you got a second?

Amy Buechler [45:23] – Yeah, I know, totally. Being explicit and intentional about having this conversation and then doing a little bit of prep and sitting down and literally even writing out a script for myself if necessary where it’s like, “Craig, I know you’ve been blah, blah, blah, something, something, podcasts, podcasts and unfortunately we’re going in a different direction and so I need you more here.” Or I’d redirect your energy toward this, but then also explicitly say, “Starting at this date, we’re no longer going to have the podcast.” And so again, 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.

Michael Seibel [46:07] – Weirdly that structure is a little mid more CEO to employee. How does it change when it’s co-founder to co-founder and maybe, there are certain CEO to co-founder relationships that are hierarchical. We see a lot at YC what’s kind of not. What’s like three co-founders and someone has a CEO title. They are like there I don’t really…

Amy Buechler [46:32] – You tell me like in my mind, I don’t know if I’d give very different advice and I’ll tell you what like I’m assuming, say we’re co-founders, say we’re co-founders okay. In my mind that 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, “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’s just an experiment, but it doesn’t degrade our relationship.

Michael Seibel [47:12] – And what if Craig thinks he’s got great point as why the podcast should continue doing this as. You know what I mean, in that situation where it’s like I think like I’ve had those conversations where the person has kind of gotten it. Like you kind of make the case and the person, you know sometimes having the conversation is like thinking about the conversation’s more painful than having it. And the person this side is like, “Yeah, the podcasts hasn’t been going well.”

Craig Cannon [47:38] – Well they’ve been avoiding it too.

Michael Seibel [47:42] – But there are other situations where Craig would say, well no, the podcast has 10,000 listeners every week. This is an important part of our brand. This is part of our strategy. There are other situations where it’s actually more of a question in fact.

Amy Buechler [47:56] – My response to that is ideally, you would already have roles and responsibilities outlines. Which I would think that would solve whatever this hypothetical question is, where Craig would get to decide what the social, what we’re doing socially and we’d have probably cleared that in advance. We’re all in alignment because it’s directly linked to whatever our company goal is.

Michael Seibel [48:19] – That’s a really good point.

Craig Cannon [48:20] – To me it kind of sounds like it’s possible the metric changed. Or if you didn’t have a metric in the beginning, then you messed up. But if it was neither and then it’s just a matter of tastes, then it gets really tricky.

Michael Seibel [48:33] – What you actually mean, if you’ve assigned roles and responsibilities, you shouldn’t, like if the roles and responsibilities, like Craig is figuring out the social media strategy, then either you trust him to do it and then it’s his test that runs the show, or you don’t, and you’re moving the role. You are removing the responsibility.

Amy Buechler [48:51] – That’s exactly right. Because you’re, before we realize this you would be micromanaging Craig and of course Craig wouldn’t take well to that, but it’s not your place to be doing that anyway.

Michael Seibel [49:01] – That’s a really good point.

Amy Buechler [49:01] – And this is that I actually see that dynamic all of the time. The other thing I would say in regards to something you said a while back is say you do whatever, remove podcast from Craig. So sorry about your life Craig. But you can tell that Craig has like weird crinkly feelings about it, but nope, like he’s not saying anything. Always ask, “How are you feeling? 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. I don’t want to be the bad guy, but like tell me what’s up.” You kind of like put your friend and colleague hat back on. You check in with them personally, and give them an opportunity to share, however they felt about how you were. And so that gets all the creepy crawlies out of the closet and you can smash them together and then you can walk out of the door and apologize, whatever, take care of the feelings and get back to work.

Michael Seibel [49:49] – It’s funny because even in this example, we kind of illustrate what happens in a startup where it’s like we almost pre-assume there weren’t roles and responsibilities. The solution was being clear about that upfront. And I thought that conversation is a more collaborative conversation. The who, what our roles and responsibilities are, is a more collaborative founder conversation.

Amy Buechler [50:09] – And again, ideally each person’s role and responsibility is linked back to that company wide metric and the goal.

Michael Seibel [50:15] – And their skills.

Amy Buechler [50:16] – And their skills. Exactly.

Michael Seibel [50:18] – So it’s kind of much more of a, like you said before, it’s a dispassionate like resource skill matching as opposed to like a power distribution, yada, yada, yada.

Amy Buechler [50:26] – Right, and also knowing that maybe every six to eight months, that conversation needs to be re-heard again. Just given especially in the early days, probably before seed-ish, things change. Totally.

Michael Seibel [50:39] – I agree.

Craig Cannon [50:40] – Now, it’s good not to surprise people. That was the one that you wanted to get to, right?

Amy Buechler [50:44] – Oh yeah, yeah, yeah.

Craig Cannon [50:46] – So there’s one question from Jeannie McAlister.

Amy Buechler [50:49] – Right, Jeannie McAlister asks, “Wwhat’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 founders is to be brave. And that means to start having difficult conversations if they’re on your mind and you know you need to have them. And that also could mean being brave by getting into therapy and learning to sit with yourself. And the creepy crawlies of your own mind, and your own feeling space actually takes a lot of courage, and not enough people do it. Also, Jeannie McAlister is my mom. So thank you mom for the question.

Michael Seibel [51:26] – 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 at and I was just like, I can’t press the button until I don’t even know where the button is, to launch. And they would just call me and like, “Why haven’t you launched yet?” It’s so funny because there’s so much you can talk about and bullshit about and argue about prelaunch that’s just like after you’ve launched, it’s completely unimportant and the longer you spend in that prelaunch and if you are dysfunctional, the longer you spend in the prelaunch, the more it’s a perfect environment for dysfunction to grow. Whereas, once you’re launched and you have customers yelling at you, it’s a lot more clarifying of what you should be talking about, what you shouldn’t be talking about. We didn’t talk about the background on ever again after we launched. So yeah, it some ways, what’s so funny is that like, you don’t have to do any of these things to be successful. A lot of the successful companies we know are in various degrees broken.

Amy Buechler [52:39] – Absolutely.

Michael Seibel [52:40] – There’s just like these are kind of hints and tricks that help grease the skids a little, but the reality is, the bigger thing is like, did you launch your product? Do you care about the problem? Is a product solving the problem? 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 a intellectual place, but it’s really true. Is that, “It’s a lot easier to have great culture when the product’s working and the company is succeeding.” Like you just start and instead of starting at a D and having to work you up, you’re starting at a B+. That is a lot easier.

Craig Cannon [53:14] – Cool, All right. Well, thanks so much guys.

Amy Buechler [53:16] – Thanks guys.

Michael Seibel [53:17] – Thanks for having me.

Craig Cannon [53:18] – All right, thanks for listening. As always, you can find the transcript and video at If you have a second, it would be awesome to give us a rating and review wherever you find your podcasts. See you next time.


  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon