The Hard Thing about Simple Things | w/ Rob Snyder

All right, we're back.

Welcome, Rob. Somehow we're back.

That's right, they're still paying us the big bucks to show up and show up and chat. Hey, I went back into, um, the recording for last week's episode, and we attacked that with a samurai sword, like with the— our hypothesis that we were talking about before of whether virality was driven by the number of times that we say samurai sword in the episode. Um, it did not viral. However, you did make it 24 times that you said samurai sword, and if you listen to the episode, it's with like increasing inflection and enthusiasm throughout.

Great. The, the thing I realized actually, uh, as you say that is that it would have gone viral if we had hit 25. I'm pretty sure we just, we're just like off by one.

Well, there we go. There we go. We started with 2. So if we can just find ways, it's going to be harder to get it in another 23 times, but it's not beyond us. For our mailbag this week, we have 3 cease and desist letters. It turns out cease and desist letters can start with "For the love of God." And— Stop. But anyways, what's going on with— No mailbag, but leave a comment if anybody's watching this or our listener. If our listener is watching this and you want us to talk about something, leave a comment or drop us an email. Anyways, Rob, what's, what's on your mind this week? What's been going on?

Yeah, I mean, given that this is obviously blowing up and everyone's, everyone's talking about the podcast, I figured what we probably should do is explain what the hell we're doing here and, you know, what are we trying to accomplish by doing this? And I think the core thing that I have observed as a founder is that most startup advice sounds right, feels right, and then when you put it into practice, it is so wrong as to be confusing and backwards. And you just wind up like, like I did, spending years just hitting your head against the wall, making no progress, doing a bunch of things that seemed like they should work. And so I've just kind of been obsessed with why do startups work when they work. And so everything I read about, whether it's the book, whether it's the newsletter, whether it's random rantings on, on LinkedIn, and this thing where we're talking through it, is to try to push forward and develop like an actual theory, an actual set of frameworks, theory, How does this startup thing actually work? Why do they work when they work? What are the mechanics of it? And we're gonna try each week to push that forward in some way, shape, or form. And so that's what we're doing here. And if you are interested in startups, this is for you.

Yeah, I like that. And having been there for your pain cave, like a bunch of phone calls where you were like, you know, this is the crazy stuff that's going on. And, you know, excuse me, random points where you were trying out Agile, you were trying out different product ideas, and then, you know, coming back somewhere between 2 and 6 months later being like, well, that didn't work. And the growing— it seems like that's where this kind of passion inside of you was born, just like out of that frustration from banging your head against the wall with your first startup?

Yeah, just like a growing smoldering rage at what we had learned in business school about startups, what I had read in all the books, all the things that we were told to do. Again, they just all made a ton of sense before you actually tried to put them into place.

Yeah, and what's an example of something that you tried to put into practice that sounded right, didn't work?

Yeah, I mean, I think like one that I'm gonna rail against probably in more detail next week is discovery interviews, which are things that you're told to do. You're told to interview your potential customers in an unbiased way to try to figure out what their problems and pain points are and figure out what you can sell them, right? Which sounds like it makes a ton of sense. There's a ton of books and frameworks and processes about how to do that. And In my experience, they don't work and they're not even a good process to figure out what to sell and deliver.

It's not a terrible bridge into this week's content. We're talking about the hard thing about simple things from Rob's newsletter. Rob, what's your thesis for this one?

Yeah, so what I'm trying to— what I've kind of realized and what I think everybody kind of knows in the back of their mind is that in order to find product-market fit, you need to try to sell something. And it's just like that simple. And the process of trying to sell something helps you figure out what you should be selling and what you shouldn't be selling, who you should be selling to, who will pull, who won't. And so it's like a— it's a relatively simple thing. The, the thing, the work you do, yes, there is nuance, yes, there's complexity to it, but we make it out to be way more complicated than it is. Like, I see, I, I talk with so many founders and I'll see, right, there's like a 40-page market thesis document, there's a spreadsheet that has like 10 different sheets to assess market size, competitive wedges, and you know, like all this kind of complicated stuff. And, you know, they do hundreds of discovery interviews and all this kind of stuff, and it's like in the end they haven't really figured out anything, and a lot of this stuff has kind of wasted their time versus pushed the business forward. And so there's a question of why is that the case? Why do we do these things?

So last week with Tollbooths and go-to-market, we were talking about post-product market fit. Like, how do we, how do you like really go after go-to-market when you're kind of like already found product market fit? Now we're in, we're back in the pre-product market fit. You're trying, are we like pre-idea, post-idea? Like, where, where would you center us on this one?

Yeah, I would say like we're in the idea stage trying to get from idea to customers to product market fit, and it's But I think this observation kind of scales across stages too.

Okay, interesting. So let's take the, you've got, you know, a solo founder, maybe you've got, you know, a couple co-founders. They have an idea for, I don't know, is there one that comes to mind? We could pull a random B2B SaaS idea. Or something. Okay, AI workflows. What does it look like in kind of like the popular approach to doing this?

Yeah, so like you just take, I mean, what would you do in when you were at Bain, right? Like what would you do in that situation?

Yeah, market studies, try to get anybody on the phone that I could. I'd try to probably like read about it, think about the macro. You know, figure out if it's worth my time, essentially. Like, is there a return on this thing? Talk with people that are from the industries that I'm interested in selling to, to try to understand. Yeah, like, how are they using AI? Like, I'd probably record a bunch of that stuff, take notes, debrief with my team.

Yeah, is that like— yeah, that's like, that's generally the kind of work people do, and that's, that's fine. But then what happens after that is you wind up with a, a Bain Co. deck, right? That's a 40-page deck that's, here's our market thesis, we're gonna use that to go raise money, we're gonna use that to go build an MVP, we're gonna use that to do XYZ, right? And like, you still just haven't figured out, is there actually demand here? Are people gonna pull? Or can we sell something? It doesn't even need to be a product yet, but like, We know we need— in the back of your mind, as you're doing all that work, you're like, "Yeah, I'm being productive." But in the back of your mind, you know, like, this isn't real. This isn't real yet, and there's that sinking voice in the back of your mind that's like, "Are we just wasting our time here?" Yeah, let's get into that.

You outline it at the start of the blog. You talk with potential customers. And see if they buy, aka try to sell. When that doesn't work, figure out why it doesn't work and change something, which you refer to as debugging. And 3, if it does work, if you do sell, try to deliver and make them not churn. That simple, that straightforward.

That's essentially it. And there's some nuance to it, like how do you know who is a potential customer? How do you actually talk with them? Again, that's what we created the PULL framework for, which is like, who would be weird to not buy this? Okay, cool. That's useful. But even if you're just hitting your head against the wall trying to sell to potential customers and you just listen and you figure out, okay, we had 5 conversations this week, 1 person was actually kind of interested, 4 thought it was the dumbest thing ever. What's the difference between them, right? And you just do that. You can start to figure out who actually has demand, what is it, and go from there. Like, that is the process. And it's like way less elegant than creating a deck and solving it all in your head in advance, but it's actually way more likely to get you to the right answer.

Well, let's talk about why this is hard. Like, you, in the, in the blog, you talk about the, What is it like increasingly flexible or athletic ways that founders avoid this? Like, why is that the instinct to like to not sell? Is it, you know, I think a lot of it has to do with like rejection. Like you feel kind of like an idiot when you start out and that's like, ooh, you know, stay away. But why do you see founders trying to avoid the simple steps?

Yeah, I think it's, I do think it is a bit of rejection. I think there's a bit of feeling like sales or going in person, whatever the thing is, that's the simple direct thing, right? It's uncomfortable or it feels like it's beneath us even sometimes. So sales is typically both of those, right? Sales is both uncomfortable and a lot of, you know, consulting type founders, MBA type founders view sales as something that other— we hire people to do. And so we don't do it and we procrastinate. And the way that we procrastinate is we create a lot of complexity around us. And so we create a bunch of work that seems important and urgent, but it's really just kind of paper shuffling. And so we wind up working 70, 80-hour weeks or whatever and like making literally no progress because of it.

Yeah, and you know, in addition to it feels beneath us, which I, you know, having come from that consulting background, it's like we talk about high strategy as if that is like God's gift to the business world, and many companies need strategy, but that's really not like, there's so much else that's more interesting and more important. But also, I think going into sales, it was like you needed to have like sales training, like there's a special way that salespeople talk. There's like a magic almost that you prescribe to salespeople that you're like, I don't, I don't have that. I'm not like the charismatic person that is in this, so I shouldn't be doing that because that's my skill set is looking at numbers and making PowerPoint and other people should sell.

Yeah, it is a, yeah, underneath that though, there's like a, I look down on sales.

Yeah. Yeah. Let's talk about the barbell analogy that you work in.

Yeah.

Yeah.

So this, I think, is like one of the cool things, which is, I don't know, it's just, it's interesting to find weird analogues that I think actually help you see reality. So like, example being, I had always, you know, I always worked out, lifted weights, and have a basement gym, which is awesome, right next to this room. But like, I was just like working out and not getting stronger. You do all these fancy workouts, you follow all the routines, and you're like, you don't get really strong. And so I stumbled across this guy, Mark Ripatoe, I think that's how you pronounce his last name. His thesis is like ridiculously simple, which is in order to get stronger, you need to lift heavier weights. I'll just wait and see if that makes sense to you. Is that a sentence that computes?

For me? Yeah. Uh, yes. Like that's, um, it's like, like just, Pick up heavy things and your body will adapt to that.

Yeah, exactly, 100%, right? And it's so obvious when you say it like that. And it's like, okay, so he basically creates this workout routine that is deadlifts, squats, shoulder press, bench, maybe something else, I don't remember. And it's like, you're gonna do 3 sets of 5 and then next time you're going to add 5 pounds to the bar, and that's the workout routine. It's like, oh, obviously that would be the workout routine because remember, to get stronger you have to lift heavier weights. Okay, cool. And so, so then in my mind I'm like, why is this simple thing— why haven't I been doing this simple thing? And you realize that the moment you're looking at the bar in the morning when it is the heaviest weight you've ever done and you're looking for any excuse to not do that very heavy weight. Yeah. And that's when you realize that it's like, oh, the function of creating this complexity, of doing all of these different kinds of workouts, is to avoid the simple hard thing. And that's when it clicked for me too, which is also a form of procrastinating on lifting that heavy weight. It clicked for me that this is the same thing we are doing in startups generally. This is, this is why work just metastasizes in a way that prevents us from doing the simple things that matter. We see our version of the heaviest barbell we've ever seen And we look at that and say, I don't want to do that. I don't want to sell. I don't want to call the customer who churned. I don't want to go in person. I don't want to go to the conference. And so instead, I'm going to do this massive amount of work that's not actually moving us forward. And like, mm, I realized I do that. I realized it when I was looking at that barbell, and then I realized, oh, Maybe that's why we all, we all complain about being so busy and aren't moving the business forward at all.

Yeah. That is super interesting. As somebody who is going through almost that exact thing right now with, I've been putting off, um, yeah, a new, a new, uh, program and like the actual design for so long and finding like, I just do the things that I want, that I enjoy doing about my work and have for the last month been staying away from the part of my work that I like actually need to do because it's the revenue generator and what we do. Yeah, the— and for anybody that's not a weightlifter, like, I think about that with triathlons. I did an Ironman a couple of years ago and it was not heavier weight every day, but basically every week for a very long time. You are looking at like, oh, it's 5 minutes longer on the bike, or it's a 10-minute longer swim, or now you're stacking them on top of each other and they're just increasingly painful, like boring actually. Like boredom is a really big thing with, uh, with endurance, the ultra-endurance stuff. Uh, and so it's, yeah, just like whatever you can do. I had to simplify everything in my life in many ways. I had to cut out basically any reason that I would have otherwise given myself, um, to not do the work. And that made, made it so that I actually would, you know, start swimming or get on the bike or start running. Yeah.

But let me, let me ask you there too, like, so this, the kind of simple truth about getting stronger is you have to lift heavier weights, right? And just keep doing that. Is basically that simple truth about ultra marathons and whatever. It's just you have to do more distance.

Yeah. And there's, there's some things that don't translate exactly, which is like recovery time with, with your body. But essentially, like, you do these— there are workouts called BRICKs, which are, um, it's a, it's a bike to a run, and you're really working on that transition for the, the latter part of the triathlon. Um, and the BRICK over the year that you're training, a year and a half or 6 months or whatever, keeps getting longer and more intense until eventually you're doing like, for me and my, the training regime that I was on, it was like at the end it would be like a 6-hour ride followed by, you know, a 10K or 15K or something like that. Or a 5-hour ride followed by, you know, you're just like getting off the bike and starting to run. And you can't start there, you have to like, there are so many incremental, you know, in your case it's, there's 5 more pounds on the barbell. And in that case, it's like, this is just gonna be a longer workout that you have to build to because it actually connects to the end of yours, and I'll get there in a second. But you know that eventually that, you know, you're gonna be standing there on the starting line and it's gonna be the real thing, and whether or not you trained was gonna be the only thing that mattered.

But have you also seen, like, I assume, and I feel like you've talked to me about this too, that there's a ton of advice and like a bunch of best practices out there and a bunch, like there's basically a bunch of things out there that are just trying to avoid the simple truth.

Yeah, I think, and equipment, I think like for like the cycling community is where it's a better bike. It's, you know, carbon fiber, whatever wheels and frame and Nutrition, like there's a bunch of just like really unnecessary complexity out there. It's like, oh, this is actually quite simple. Your body needs to be able to move for a very long time and your fueling needs to be able to maintain your body moving for that long. And so the fundamentals of, of that distance of race are quite straightforward. But yeah, it's I think very poorly understood until you have to spend time in it.

Yeah, yeah, I think the same is, the same is true of extra, like, the lifting and whatnot. You just, you can get, you can always think, oh well, maybe if I get a new training regime, or maybe if I like try this new workout video, or whatever it is, then I'm gonna, I'm gonna get stronger. And it's like, put, just put 5 more pounds on the bar every time. That's it. Do the simple things, 3 sets of 5, that's that.

Yeah, inescapable, just like weight. And it's actually kind of, it's surprising how short a time, in that case, you're in discomfort, or even like the triathlon workouts. It's like you start moving and it's fine, but it's like there's this period of intense mental, what can I do to get out of this, before it. But it applies also to sales conversations, like I would, I would do everything I could that, you know, in the time leading up to like actually 2 hours, just start cold outreach, get on the phone. In my case, I was calling universities and wildlife nonprofits. And, but I would do like, if I didn't specifically, if I didn't get started, I would do anything I could to not do that.

That is, I think that's the thing behind why startups feel so complicated and why there's so much complicated advice. A lot of the complicated advice comes from people who just won't put 5 pounds on the bar every lift. And a lot of the things that we do are trying to avoid putting the 5 pounds on the bar every lift. Finding product market fit, selling, like going and seeing customers in person, doing the obvious things. The reason we don't do them is not because this is a fundamentally complex thing. We don't do them because it's an uncomfortable thing.

Yeah, totally. Discomfort, like small discomforts, the extremes that we will go to to avoid small discomforts. There's a couple takeaways that you have in there about like what do you advise that startups do. I'll read through these 3. It's, you know, 1, accept that simple things apply to us, know the alternative, and have something that pulls you. Into the simple work. Let's talk about, like, what do those mean?

Yeah, first one is the simple things apply to us. We have to add 5 pounds to the bar. We have to sit in the saddle longer on bike. We have to sell. So the main reaction I get whenever I talk at Harvard, MIT, whatever, the main reaction is, I don't think this applies to me because, right? Because I'm B2C, because I'm enterprise, because I'm deep tech. It's as if, Like, we're just looking for some reason to be immune from the uncomfortable stuff. Maybe, maybe we can go and sit in a room and build what we think the world wants, and then the world will shower us with praise. And it's like, yeah, probably not. Simple things generally apply to you. Put 5 pounds on the bar. Okay, that's, that's thing 1. Thing 2, what I've realized is that most of the people who will listen to this and Anne's us, right, we've done everything right in the past. Like everything has kind of worked out for us. Wound up at HBS, wound up in consulting. Like, did you ever get a B? I'm pretty sure you never got a B.

I got one. I got one. But yeah, it was—

I actually only got one in my life, so—

Neither you nor I were particularly good at business school. So if they would have given Bs, I think that's where we would have fallen. But anyways, keep going.

So yeah, because stuff has mostly worked out for us, we just like inductively assume that this startup thing will probably work out for us. No, kind of, you know, it's all worked out in the end for us. We're here, we're here now, so it'll work out for us. And that is not the case, right? If you don't do the simple things, you will die. If you do the simple things, you might not die if you do them with intensity. And so it's— we often think, oh, it's just going to work out, so I don't have to do it today, I don't have to do it right now. This doesn't apply to me. It's like, no, do them now.

Yeah, yeah, there's— this is semi-unrelated, but an analogy you gave about starting a business was, you know, when you, you leave Google or you leave McKinsey or whatever, and you think that you're going from bowling with the bumpers on to bowling with the bumpers off, but you're actually— you have to build the bowling alley. It's like you were just like in the middle of a parking lot that probably has some trees growing in it and stuff. And you've got to like, it's the level of complexity and uncertainty. And the, you know, the certainty is failure. Like that is the outcome of not doing the right things.

Default failure, right? Default is failure. And it's rare to break that default.

Yeah.

Yep. And so you have, but, and it's, it's impossible if you're not trying, if you're not actually like doing the uncomfortable thing.

Yeah, and especially if you, if you increase the complexity by, you know, 10x, and it becomes more expensive.

You wind up building a product, you might wind up making work for the product team instead of doing the simple things, right? And you're just burning a ton of money and not sleeping at night. It's just terrible.

Yep. Let's talk about the third one, something that pulls you into the work. What do you mean by that?

Yeah, so one of the things I've realized is, especially in startups, when I say you have to sell, or when you accept that you have to sell, you can't show up and just say, well, I'm showing up to do my sales work. I hate myself. I hate this work. Like, this sucks, right? Because yeah, you, you're showing some discipline there, but you have to actually want to win. Right? And you have to, you, you have to want to win more than you want, than you like dislike being uncomfortable. And so what I've found is for me to get over the fact of like, I don't like to make 50 cold calls in a day. Well, I'm going to do it because I have to do it, but I want to be great at it. And in fact, like I need to find something in the work that pulls me, that causes me to like say, yeah, that discomfort is nothing. That discomfort isn't even relevant. So for me, it's just like, how do I solve this riddle of demand? How do I find somebody who actually pulls? This is a, this is a really interesting problem to solve, and I want to solve it as quickly as possible. And so that's what pulls me in the work versus just focusing on the discomfort.

Yeah, that's interesting. What is— do you— how do you see that manifest in other in other founders?

Yeah, I think of it as, like, I've seen founders who either do it because they just are really, really angry about the thing that caused them to start the business, right? It's just pure rage. There's a, you know, like, I'm a first-generation immigrant, and if I don't solve this, right, like, I have no fallback routes. That's a pretty compelling one. And so what pulls them into work is like, this is my only path. And so yeah, I don't care if I'm going to get on a phone, like, doing sales work, great. If it's going to get me there, I need to do it. And then there are people who are like, you know, this is, I really want to serve this particular kind of customer. And figuring out what do they need is actually a really cool intellectual challenge and designing something that that is like so awesome that they thank us for exist— they don't just buy, right? They rip it out of our hands and tell everyone they've ever known about it. And that way I can be in the pantheon of entrepreneurs. Like, that's another cool thing to pull you in the work.

Yeah, I identify to a certain extent with all of those. The, you know, the one that you bring up about the immigrant, like with the triathlon, it was like I knew that on October 21st I was was like gonna have to start. And so there was a deadline that I was going to eventually run into, and so the work was unavoidable to a certain extent. But with startups, that often doesn't— that's not the case. Like, you don't have like in a year and a half, but like, I guess there's that.

Yeah, that's a, that's a far away— that's often a far away thing. 6 months out, 6 months is so much time. Or 18 months out, we raised a million bucks, we could like That doesn't seem to do it. There seems to be a moment, you know, maybe 3, 6 months out from cash-out date where there's a reckoning, like a mental reckoning. But you want something before that. You want the hunger to figure it out. And it's sometimes it's greed, sometimes it's like fear, sometimes it's something that's genuinely curious for you. But like, it's got to be something that pulls you that makes the uncomfortable work not so obviously uncomfortable.

Yeah. How about like tactically? What takeaways, what things would you say founders should do like with this?

Just look at your week. Look at your calendar. Look at what you accomplished this week and ask yourself, was like, what of this was actually pushing us forward versus what, what of this was work that I did to avoid the work that mattered. And then put 5 pounds on the bar. What is—

instead of letting us end there on that poetic, poetic termination to this, what is putting 5 pounds on the bar like, look like for a founder? Like blocking off your calendar or starting to call?

Like, it's how are you going to talk to 5 to 10 potential customers next week? If you're doing that, great. How are you gonna improve your conversion rate? If your conversion rate's fine, cool. How are you gonna make onboarding work? Like, what is the bottleneck in your business? We talked about this a couple weeks back, right, with the Case Study Factory. The bottleneck is the simple thing that you need to focus on. Usually it is, we're not talking to enough potential customers. That's like the majority of founders. We're not talking to enough potential customers. We're talking to one a week. You're never going to learn fast enough that way. Okay, cool. Get to 5. Get to 10. Nothing else matters unless you do that. That's putting 5 pounds on. Then solve the next thing.

Love it. Love it. Um, anything else on your mind, Rob?

No, this is one I've wanted to write for a while because I think it's, uh, for me it was really satisfying to write this. I have no idea if Like the Venn diagram of like heavy barbell lifts and entrepreneurs has to be like exceedingly small, but there's gonna be like 3 people who love this one. And so that's really something for you. Yeah.

Um, there's gotta be other, other analogies that we can work in next time. Um, we're also gonna be putting this on Spotify, so we'll get the, we'll get the links in there. Um, if anybody is tired of staring at us and wants to get the audio version. So we'll have an RSS app. Yeah.

Cool. I have the face for audio and the voice for news articles.

Yeah, that's right. We'll get an AI avatar one of these days for both of us.

Please God.

Yes. Awesome. All right. We'll see y'all next week.