Join us in this episode, where we sit down with the remarkable Waseem Daher, a serial entrepreneur with a track record of turning startups into gold. Waseem shares his invaluable experiences and strategies that have led to the success of his companies, including his latest venture, Pilot, which has gained backing from the likes of Jeff Bezos.
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Key Takeaways:
Waseem's journey is a testament to the power of a clear vision, a strong team, and the willingness to adapt. Whether you're a budding entrepreneur or a seasoned business owner, this episode is packed with insights that could change the way you think about building and scaling a startup.
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Andy M:
What's like your strategy for when, like how you start a new company?
Waseem Daher:
It starts with the team. The first thing for the company has always been, who are the people I want to do this with?
Andy M:
Solve a problem that you have, because I always say like, if you have a problem, there's probably a million other people at least that have that problem.
Waseem Daher:
Yeah, it's a cheat code, right? Why is it your final startup? I think we have all the elements. We have an amazing team. The business is well capitalized. It has great traction. And as we just talked about, the like scope of the vision is so large.
Andy M:
Let's see. Hello. How are you doing, my friend? Good. How are you? Doing good. Doing good, man. Like the first question that I had, and we just get into it. I hope you don't mind. I like to make it conversational and just like, like people can kind of like feel us meeting for the first time too. And so, um, I think that the big burning question that I have for you initially, which I'm, I'm sure people might ask you this a lot. I listened to a couple of podcasts before this with you on it is, Man, everything you seem to build turns to gold, right? So far. Yeah, so far, so far. What's your strategy for how you start a new company? Do you have some sort of mental framework or decision process? Are you just like, as simple as, hey, this is a need in the market that we've found and let's do it kind of thing. Like, what's that look like? Yeah.
Waseem Daher:
To answer your question, look, I mean, it's really about like, it starts with the team. The first thing for the company has always been, who are the people I want to do this with? Because that's really what your company's experience is like from a day-to-day perspective your company's experiences You're spending a bunch of time with these people trying to make this thing happen So you have to feel like you have high conviction in the team The team's capability that you want to spend time with the team that you're excited to spend time with the team. I So for me, it has always been about the team first and foremost. And actually, when we started our second startup and our third startup, it was the same founding team, essentially. And it always started with the team. We got together. We said, OK, we want to do another startup together. What is it going to be? The team was the constant. The team was the first thing we dialed in on.
Andy M:
You guys knew you could mesh and work together. And yeah, totally.
Waseem Daher:
After that, I think the things we look for like big market size, like is the opportunity really, really large. And the benefit of the market size being large is it just gives you a little bit more leeway. Like, you know, If your market is small and you have to capture a huge percentage of it to make it work, it's very sensitive to kind of those initial assumptions. If the market size is large or growing and expects to be large pretty soon, you just have a little bit more breathing room to figure things out. Maybe your initial thing was not exactly right, but like a slight adjustment to it would still land on something that's big. So I'd say market size is a big factor. And the third is really just trying to very anecdotally validate the need, meaning let's go and talk to, we have some hypothesis about who we think the potential customers are. Let's go and talk to some of them. And let's see, is this really a hair on fire problem for them? Is this really like in their top three? And if it's not, then it's probably, I'm not saying it's a bad business, but it's not a business that I like to do. I like to do things where just like the pain is so glaringly obvious for someone that it is in their top three. And it's like, cool, if we could solve this for you, would that make your life better? And they're like, oh my God, yes.
Andy M:
Where do I sign? On one podcast I was listening to you in the past, you were saying, that you almost these pains or pains that you had in your own businesses since the since when you started building businesses. Right. And which excuse me, I thought was interesting because I have this framework of like I've thought about this and started a couple not as successful as yours yet. Yes. Yes. This next one, though, it's going to happen. It's going to happen. So with that, I think there's like, okay, solve a problem that you have. Cause I always say like, if you have a problem, there's probably a million other people at least that have that problem. Yeah.
Waseem Daher:
It's a cheat code, right? I don't think you have to do it, but it makes your life a lot easier because the first thing you're trying to do is to figure out who am I targeting and what should I build? And like, if you have the problem and there are lots of people like you, That's kind of like a built-in initial market that you know a ton about. It's like free customer discovery work that you don't otherwise have to do. So I don't think it's a requirement, but it makes life a lot easier.
Andy M:
Yeah, 100%. And for me, I feel like it keeps you... One, it's more like empathetic building because you're kind of like, Ooh, that could be like a book title or something. It's like empathetic, you know, entrepreneurship or whatever. So you're like building for yourself. And then two, I think it keeps you motivated because you're like, I freaking, you have conviction that it's like, yes, I know this is a problem because, hey, I had the problem. And I think a lot of people, buddies that I have today, you know, that maybe haven't built anything in the past and stuff, and they build like a solution and look for a problem versus like, look for a problem, build a solution, right? And so I see that happen time and time again. And like, you seem to avoid that, which is pretty awesome at all costs. And so, so yeah, my question for you is, when you experience your own problems, there's probably for me, even right now, building a new company, I'm like, Oh my God, there's like 10 problems here that like, I wish there was a better solution for, you know, as you're building, you get those ideas. How did you decide which one to pick? Right? Was it like, do you get the team together and do you say, Hey, let's vote on what we should do? Or, you know, cause you have the team in place or was it like, Hey, we all agree. This is the most pressing thing that most businesses and the biggest market size opportunity.
Waseem Daher:
It's definitely closer to the second one, meaning that you're never going to have perfect information in starting. And so if your bar is, I've done some super rigorous analysis and I made all the charts and graphs and the numbers imply that XYZ is the right business, that's not going to happen. all of your business ideas are going to seem bad. Because anything in the early days, it's like, well, maybe this is a good idea, or maybe it's just a bad idea and that's why it doesn't really exist. You basically, you and your co-founders have to kind of get together and say, well, look, we don't know, but we're kind of leaning this one. Let's give it a shot. So I don't think there is a perfect mechanism or system with super high conviction determining which one is the best one. There's a certain amount of you just have to... It's like an exercise of the head and the heart. You just have to be into it, I think.
Andy M:
Yeah. I get it. I get it. And what got us this conversation, which is fun, is I actually became a pilot customer for Distribute. And you personally emailed me And you actually said, hey, I am. This is actually me, Waseem. I am emailing. You just want to say thank you. And I was like, oh, and anyway, after you email me, I actually emailed you back. And I was like, I was like, is this really you? I was like, I'm going to test it. So, you know, I'm going to test this. And I guess it's really the same. And you respond. I'm like, OK, this is really the same. This is awesome. And so I'm like one, either Waseem is like really on top of this whole founder led sales thing and like really like in the weeds or two, they're not adding a lot of customers. So I think it's one.
Waseem Daher:
It is number one. I send a lot of these emails. I mean, look, the thing that's funny, you have me on a little tangent about this now too, which is like, look, my background, I studied computer science at MIT. I was an engineer by training, like in our first company we were like, Oh, we just need to like build the product and like that will like solve all our problems. And we learned kind of very viscerally, like, No, it kind of doesn't like the product needs to be good, but the product being good is not sufficient to get it out into the market. You have to really make the case to people about why it's good and why they should be using you. And I think one of the secret weapons that any founder has is you just like care a lot. Like you care more than most people care about the things they do because you're the founder, right? You're like one of the founders of the company. You started the thing. And I think if you can like channel that care into things that make the customer experience like really good or differentiated or feel like honestly not scalable, Like that's very powerful. Like look, we have literally thousands of customers. So we do add like a bunch in a given day, in a given week, in a given month. But it is not so many that it's intractable for me to look at the list of them and send them email. And so I do. And at some point, that won't be possible. At some point, like, no, it will not be realistic that I do it. But like, most people wouldn't because they think like, oh, it's not scalable. But it's like, actually, it doesn't matter if it's scalable. What matters is you can do it now. And I think it really helps. Like, I think it's a valuable signal to the customer that like, look, we care. We're gonna like do our darndest to like really make it work, you know?
Andy M:
Yeah. Yeah. And in It does come across that you care right and that and it's so it's something so simple to in like some people that I you know is it like that they think they can't do it is it. It's like do you care or you just lazy you know like do you just not want to do it like. And a tangent now you got me on is you were an engineer and you went into sales. Cause that's my story, right? I studied electrical engineering. I was an electrical engineer, did like power systems and electronics engineering, hardware. So if anyone listening don't do, hardware is insane. Go do CS. Skip the hardware. No, we actually need hardware people. But, did that, and then I went into sales. So I was early at outreach, right? And I started more on the technical side. And then I ended my career at outreach and enterprise sales. And what actually made me want to do that, and this is so like Silicon Valley tech of me, right? But it's like that one Naval quote, which was like, learn to build, learn to sell. If you can do both, like you'll be unstoppable. And so I was like, shoot, yeah, like I've always been a builder. I'm pretty okay, above average at building things, I would assume. but like there's what's it doesn't matter. Like at the end of the day, like how good your product is, because if no one knows what it is, it's not, especially, and it's getting harder and harder and harder and harder. Right. And so that is what propelled me to really do that. And kind of like do the sales thing. Right. And like learn it at like the, you know, the master's level of like doing it for outreach at a sales company, selling to salespeople, doing that whole thing. And I wouldn't trade it for anything. Right. Like I would, I would never go back to being, no, I just want to do engineering or product stuff. Yeah. And now could I have been like an A plus star engineer if I stayed in that side of the world? Maybe, but I'm also thinking like, and I want to get your thoughts on this. Is it better to be a generalist or is it better to be like super hardcore in one area?
Waseem Daher:
It's a good question. It's a good question. And I think it really depends because like as a founder, you kind of do need to do a little bit of everything. And so in that sense, like being a generalist is more useful. Look, I think there are two options. Option one is, let's say just kind of classic structure. You have two founders, right? One is the builder and one is the seller. And they're actually like, you would rather the builder like be spiky at building and like have amazing chops on building. And you'd rather the seller like be an all-star seller. That, I guess, is an argument in favor of specialization. The argument in favor of being a generalist is like, look, for the VC-backed, high-growth startup, your main lever for getting things done, hopefully, is not you literally do it all yourself. It's hopefully you like find and hire and attract and retain good people, people that are amazing at what they do in each of those disciplines and they do it. And so that actually is an argument of fair being a generalist, which is like if you can talk to the sales reps and you can talk to the engineers Like, that's very powerful. Because, like, you now, like, you're credible in both worlds. Whereas, I think if you just, you're like, look, all I've done is engineering forever. I don't know anything about sales. I might not even respect sales. I might think that, like, sales is icky or bad or not valuable or not hard or whatever. Like, that's gonna be a problem. Like, that's definitely gonna be a problem. You have to kind of, like, get and appreciate and value what the function does. to be able to successfully get good people to do it with you.
SPEAKER_01:
Yeah.
Andy M:
Yeah. And with that, obviously, you're big on founder-led sales. How did you break through on that? Were you just like, I care so much that I'm just going to freaking do sales for my companies? Or did you read all the sales books? How did you get started with Siemens? And was it scary? I'm sure you were scared. You're like, what the hell am I doing here? Right? It wasn't easy.
Waseem Daher:
Totally. Yeah. Honestly, a little bit of all the above, which is to say, so in the first company, the first company we started, we started right out of school. It was four of us. We were all engineers by training. And it was very clear to us in the early days, okay, we need to split up. We're not all going to be able to write the code. Like some of us will need to like do sales and marketing and products and some of us will need to like write the code Like who's gonna do what and I like liked writing the code. I like quite enjoyed being an engineer But I was like, well, I kind of like talking to people too and like the good news is It was a highly technical product. We had technology that could update running Linux systems without rebooting. We would go and basically live patch the kernel. And so we were selling to IT admins and developers and Linux nerds, basically. And so actually, it was a nice entry point into the world of sales because what you were doing, and this is, I think, when sales is done well, this is what you're doing. You're basically understanding what problem they have And you're thinking about, well, does my thing solve this problem? And if so, let me explain to you why. It's super consultative. And I think that was helpful to me. That was really easing my way into it because it's not like we were selling a commodity thing and I was just trying to get you to pay as much as you possibly could for it. It was like, we have this technology. I thought it was cool. We were proud of it. We thought it really solved the problem you had. I wanted you to use it. And we would geek out together, basically. And so my entry point into the world of sales was actually not like, oh, I have a quota, let me sell you these things. It's, we have a thing, we're excited about it. We're excited to like see you use it because we think it'll help you. Like as one fellow nerd to another, like let me get you on board on it. And I think that sort of led me to like, probably I could have like learned a lot faster if I had like a solid sales mentor. Like it was literally, we're Googling things like when does a lead become an opportunity or like, How do you even do sales? Like there was this like, I'm trying to remember what it was called. There was like a six page like PDF that I think came from like Harvard Business School or something. It was called Selling as a Systematic Process. And it was just like, look, it was only six pages. How comprehensive could it have been? But it's like an overview basically of like how you sell. And that was like my Bible. I was like, Oh my God, like this is okay. Cool. Like let's do this.
Andy M:
I'd love to see that PDF actually. I got to dig that up. I wonder if it still exists. Yeah, I want you to email me that because we can put it on the screen in the YouTube or whatever when we do that. Or hyperlink it and be like, this is how we'll see more in sales.
Waseem Daher:
I bet, you know, the worst part is I think it's probably even like a paywalled thing. And I bet someone like got me a pirated PDF of it.
Andy M:
So the whole thing was like extremely janky.
Waseem Daher:
It's like we were bootstrapped. We were 22. We didn't know anything about anything. The whole thing was extremely scrappy. And I think that actually also like forced some one it forced really good hygiene and two it forced us to learn a lot about a lot Because I think like, you know that the venture back started the raise a ton of money out of the gate Your first instincts are like cool. I got a bunch of money Like let me go hire people to do the things whereas for us. It was like cool. We don't have any money I guess i'm doing all the things And so I think that kind of forced us to like really dip our toes into a bunch of different aspects of running the business In a way that was ultimately I think really helpful.
Andy M:
Yeah, nice. Nice. That's amazing and For you, you're still obviously doing founder-led sales, probably not as much as you were at the beginning of the company, right? And so I think that gives you a superpower with being able to understand like, hey, maybe we don't have as much pipeline as we want. You know how to ask what questions. Totally. Right? Which is super, super duper powerful. And the question I have for you today is like, you are, actually before I ask that question, Your service is almost like you mentioned tech enabled accounting, right? It's almost like that level works. It's almost like half software, half agency. Uh, in a way, right. Yeah. And, and, you know, I was talking to him. I had this idea where I think that's where most software companies are going to have to go. Um, I don't know what your thoughts are, but I think not all of them, of course, the infrastructure, high tech stuff, but a lot of them, if you look at like an outreach, right, where we produce this, you know, this platform to, um, create a bunch of, you know, help with your outbound process, automate emails, calls, all that stuff, right? Well, it wasn't successful without us actually creating the content for the sequences and creating the sequences and the layout. And so we think, you know, I think a lot of us tend to think like, oh, we're a tech company, but there's still that level of services that you need. And it's almost more important because the software means nothing if you can't provide them with the things that they need in order to make the software successful. Um, and that's where professional services comes in and you hear this whole adoption thing. And how do you get people to adopt? So you have people helping them service them. And so is recently I've kind of shifted my mindset on that where, you know, initially you think, well, how can I just use software to automate this and do everything? And we're a tech company. We're not a, we're not like a, you know, we're not an agency or whatever. Like, how do we get away from like having to throw more bodies at each problem or whatever? And so I'm like, no, maybe I just own that and like say, no, we, we're going to need to be almost half agency provide the services. Right. Along with what we build. So I'd love to get your whole thoughts around, around that, you know, of like tech enabled versus pure software versus like, which direction should people think about and how should they think about, you know, as they build a company like that?
Waseem Daher:
Sure, so they have pros and cons and I have a blog post like on a sub stack called don't start a tech enabled service, which like obviously obviously I'm being a little cute like we did start a tech enabled service. I run a tech enabled service. Obviously I think it's a good idea, but let's talk briefly about kind of like.
SPEAKER_01:
The pros and cons.
Waseem Daher:
The pros and cons, the pro of pure software is amazing gross margin. The like incremental cost of copy is zero. It's super scalable. Like you can probably run it with a smaller team, small lean team. Like there are so many things to like about building a software product. And in some cases, honestly, if you can do that, that's probably easier slash probably the right answer. Now, the problem is usually you can't. And the reason you can't is because people don't want to buy software. People want to buy solutions to their problems. And usually the solution to the problem is, OK, well, I buy this software and then either I or an agency I hire or someone at my company or whatever, like, does something with the software to produce the outcome. And our perspective is like, HandWavy, AI, LLM, whatever. All this stuff means that there are things that used to be pure services businesses that actually can now be kind of like software plus AI plus some people. to serve that same endpoint better, faster, more scalably, more repeatably, etc. And there are interesting economies of scale there. A fake example, if I could sell you a software product like Outreach that helps out with cold outbound stuff, Or I was the best agency in the world at just like helping do it for you. And it was not like dramatically more expensive. Yeah, I would rather you solve the problem for me end to end and give me a software tool I have to use myself. So that's the pro of the tech enabled services side of things, which is people actually want their problems solved. They don't want to buy software. The big con is it's operationally a huge pain. Like your gross margins aren't as good because there are humans. It's not as consistent because there are humans. Like there's all kinds of, it's just like the matrix of like things that could go wrong or are just harder to imagine, you know, manage expands dramatically because the customer is now not constrained to like the world of your software product. The customer is constrained to literally anything they might ask you to do. And so in theory, you're like tackling a problem of like totally unbounded complexity, which is like, again, if you can do it, it's very powerful. Like you could email your pilot rep or me right now and be like, Hey, I have a question about blah, blah, blah. And like, we're going to try to be helpful. We may say, Hey, we don't do that. Or we may say, Hey, actually, yeah, cool. Like we do. Here's what you should do. But it's like the set of things you might possibly ask us about is like anything you might put in an email. As opposed to like in a software product, it's like, look, you can click one of seven buttons and like you're all, you're much more on the rails when you think of yourself as having bought a software product as opposed to, oh, I engage with this service to help me with all things accounting.
Andy M:
Yeah, that's interesting. And I'm thinking of this through the company I'm doing now, which is Distribute, because we essentially have a software to create one pagers for sales teams, right? And you can start with a blank page. And again, it reminds me of this because it's a blessing and a curse, right? It's like, well, it's like an app store and a page. So you can basically create anything you want. But that means there's so many possibilities that people go, well, what do I create? Right. What do I do? And so this is where I'm kind of like, I might have to steal some of pilots like strategy here, because I'm like, that's where I do the tech enabled service where I'm almost like an extension for the content team. Right. Because I know salespeople need more content. Marketing is underwater. Right. So how do we basically provide them a service that we get more content out that converts, but also use the tech with, you know, having someone create the, you know, maybe a writer or a designer or whatever it may be. And so that's kind of what I'm thinking. Right. And that may make more sense versus just like, here's the software, have at it. Hopefully you're creative enough to come up with something.
Waseem Daher:
Right. I mean, this is kind of like that blank page problem, which is like the implementation, getting people to actually implement it, getting people to actually use it, getting people to get ROI from it. It is much harder than just like getting them to buy the tool.
Andy M:
Yeah. Yeah. And, and for you, you know, you mentioned tech enabled and is your goal like long-term vision to keep it tech enabled or, or, or are you like go trying to go all on AI eventually, like now that you started tech enabled, are you moving towards like going all AI or are you kind of like, no, we're going to stay tech enabled as, as we move forward?
Waseem Daher:
My perspective is basically that, like, what are you buying when you buy Pilot? It's the peace of mind of knowing that someone, like, smart and competent is on the other end and is basically on your team. And that suggests to me that even if the computer could do 100% of the work, and I don't think the computer can do 100% of the work anytime soon, but even if the computer could do 100% of the work, you would still want the person there. You'd want the person there to, one, manage the relationship, two, to, like, help out on weird escalations and stuff, And three, I think if we fully solve accounting or whatever, which again, I don't think we will anytime soon, the natural next step for us is not to be like, okay, we're done. Let's all go home and the AI will just do it. It's we should do even more for you. Should we do HR? Should we do IT? Should we do recruiting? Should we help you with business insurance? Ultimately, the vision for us is, listen, if I could be your person who just did all your back office stuff, and you could focus all of your time on like the core thesis and mission of the business, that would be super powerful. And so I think for us, one, that requires a human in the loop. And two, it requires a particular type of human, meaning it requires actually like an expensive, highly skilled, smart, talented person. It's not just like commodity labor. So I think as the computer does more and more, the human, the caliber of the human element actually in some ways will become increasingly important because we will be asking them to do just the like trickiest, hardest, most important stuff.
Andy M:
Ah, got it, got it. Interesting. So as the technology improves, so does almost the level of intelligence of the human, let's call it, or the ability for them to execute and problem solve.
Waseem Daher:
Totally. In some ways, it's kind of like the airline pilot. Like the plane mostly flies itself.
SPEAKER_01:
Our pilot is very good.
Waseem Daher:
But the reason you want like talented, seasoned pilots who have tons of flight hours, who have tons of training, it's like sometimes stuff goes wrong. And when that stuff goes wrong, you want like the A-plus team flying the plane. Yeah, and again, that's not where we are today the human they like the talented team at pilot who are all full-time employees of ours Who are u.s. Based? It's like an amazing crew this up. There's a lot that we do by hand It's not like the computer is just beep beep boop boop doing everything. Yeah, even if it were like if anything I think that Increases the need to have like a really talented team of folks backing it up rather than kind of alleviating it Yeah, wow.
Andy M:
And you, I want to switch gears a little bit here because we're talking about pilot and going all and I can see your vision now you're gonna you're starting with accounting and then you're gonna go you're thinking HR you're thinking recruiting right all those services. you're almost going to be like the one-stop shop for like a lot of these departments almost. Totally. Yeah, which is awesome. And you had this, this, this is actually how I first learned about you. I think it was in, yeah, it was October of last year. And it was a tweet you wrote, which was, I sold my first startup to Oracle. I sold my second startup to Dropbox. Pilot is a unicorn backed by Jeff Bezos and is my third and final startup. If it weren't, the fourth company would be five engineers, no venture capital. And we all sit in a room together. So one, I was like, Oh my God, this is a great flex. This guy's a badass. And then two, I was like, I wonder what he means by this. Right. Like what, like obviously everything he, there's so many questions I have just with this tweet. And I think that's why it did so well. Sure. Right. The first question I have is why is it your final startup? Like, because you could probably keep going and going and going, going, I don't know, maybe you want to like become, you know, like travel the world or something, but like, Where's your head at with that? And why did you decide this is going to be your final one?
Waseem Daher:
Yeah, the way I think about this is basically like, I think we have all the elements for this, meaning we have an amazing team. The business is well capitalized. It has great traction. And as we just talked about, the scope of the vision is so large. that I'm positive you could spend like multiple decades working on this. Like the scope of what we're trying to do is so big. And to some extent, it's like, look, if we're ever going to build an iconic enduring public company, like this is our shot at it. So like for me, it's like, why would I want to do a fourth company? Like anything I could achieve in a fourth company, I could achieve here probably at even greater scale. So there's some amount of like, All the elements are here, like if we're going to do it big, this is the chance to do it big. And if we're not going to do it big, like for whatever reason, or if I decide I'm done, other people are going to carry the torch or whatever, it's not going to be because I like want to go try again. It's like, this is kind of like, I think in many ways, like the final project. And now again, it could be a multi-decade project. I'm not, I don't have particular views on how long it ends up being. I just am very, very skeptical that it makes sense to start over. Like there's so much we already have going for us here. For me personally, that it's like, this is much more interesting a platform to like build and do than anything I think I could start again.
Andy M:
Got it. And so, You know, some people would look at this and say, Oh, he just probably has a shit ton of money. You know, he's over it.
Waseem Daher:
Well, who knows? Maybe. I don't know. Yeah. Yeah. He's over it. You know, like how good the IPO is, I guess.
Andy M:
Yeah, exactly. Yeah, exactly. He's over, you know, he's going to have enough money, you know, like whatever. But no, for you, it's just like, you see the vision. And what I see in you saying that is, you're also thinking long-term about the company, right? Not like, when's our next exit gonna be? Or how fast are we gonna get to this? And like, it's more of like, no, like this thing has potential to do many other things and we can go along for that ride.
Waseem Daher:
Well, in particular, just like a quick aside on this is like, people think there's like an end to the game or there's like a finish line that you get to, and like there kind of really isn't. Like there's always more to do. And so to some extent, like if you're like, well, I'm going to just like play the game until I've beaten the game, like you don't actually beat the, even like the IPO. People talk about this all the time. They say like, look, the IPO is not the end. IPO is the beginning. There's like, and if you look at like Amazon or whatever, some of these really iconic enduring companies, 99% of the value creation is post IPO. Yeah. So it's like, I just don't think you're ever done. And if you're never done, you kind of have to proactively decide to keep playing the game and you need to be playing the game because you enjoy the journey, not because like you're trying to get to a particular milestone. I think trying to get to a particular milestone is in some ways a recipe for like being pretty unhappy.
Andy M:
Yeah, yeah, just to get some awesome. And you said your pilot is backed by Jeff Bezos. So how did that come to be? Obviously, I'm sure a lot of people ask you about that. You know, maybe you're working out in the gym with him or something, you know, because he's super jacked. But how did that come to be? I'm curious.
Waseem Daher:
Pretty randomly, pretty randomly, which is when we raised our Series C, which Sequoia and Whale Rock and some of my folks participated in. as we were kind of filling out the round, one of our investors said, Oh, you know, this is the kind of thing that like Jeff Bezos, his family office might be very interested in. Like, do you want to talk to them about it? And I was like, sure. And you don't, you don't talk to Jeff Bezos, but like he has a person who like, you know, manages this stuff for him. And like you talked to them and they were awesome and very like kind and smart. And apparently what happens is they write up, they write up like an Amazon style memo. And then just like one morning it's like on Jeff's desk, I imagine he was like sipping his coffee and he reads and he's like, yeah, Let's do it.
SPEAKER_01:
And then they do it.
Andy M:
That's awesome. Yeah, that's awesome. Yeah. You know, reading his copy, doing his thing. And then, oh yeah, this pilot thing. Yeah.
Waseem Daher:
I think he probably just has like a stack of stuff. He's like, oh, let me take a look at this. Yeah. Check it out.
Andy M:
Let's get involved. That's awesome. Yeah. That's good. And Jeff, good old Jeff, huh? Chilling on the yacht now. I think he's doing like SpaceX or not SpaceX. Yeah, Blue Origin. All right. Next point in this tweet, which is also, we're breaking down the tweet. If it weren't, the fourth company would be five engineers of venture capital. We all sit in a room together. Okay. Let's hear your thought process on this one.
Waseem Daher:
Okay. So obviously this is a troll a little bit, but I think there's actually like real insight here, which is two nuggets in this one. Nugget one is people are obsessed with venture capital. Like people fetishize it. They think like, oh, if you've raised VC, you're awesome. Like, how much should you raise? Oh, that's like how good a person you are or whatever. And it's like, look, there's more than one way to finance a company. VC has a lot of pros, but it also has a lot of cons. Yeah. And I think that like people do not, people just seem to switch off their brains when they like think about venture capital. They're like, yeah, it's good. Do it. And I think actually like it depends on what you want and it depends on what you're trying to build and it depends on what you're trying to achieve. Like we bootstrapped the first company. We didn't raise any VC. As it turns out, we probably couldn't have, but we didn't. We didn't raise any VC. We started a company in 2008. It was like dire economic times. If we wanted to spend more, we had to make more revenue by selling our thing to a customer. And that was good and healthy, and it forced a certain amount of discipline. And it forced a certain amount of real contact with reality. And I think startups in this current crop are waking up to that again, which is the way you build a successful business is you have a thing that people like and they want to give you money for. And in some ways, VC is a cheat code to avoid having to do that temporarily. You can't... He's not going to avoid it forever, but it allows you to, like, forget about that constraint for a little bit. Yeah. Under the theory that it allows you to go faster and build bigger. Like, there are obviously lots of good things about VC. We raised VC in our second company. We raised VC in this third company. Clearly, I'm, like, also pro the VC path. Yeah. But it's not the only way to do it. And I think it's important to say out loud that it's not the only way to do it. The second part of that thing is, it would be five people in a room together. One of the things that I think people don't appreciate, and this is not like, boo-hoo, my job is hard or whatever. I love my job. But the job of being the CEO of a multi-hundred person company is very different than the early days when you're starting the thing. And most people, I think, start the thing, well, most people like us maybe, because they're builders. And they want to make a thing and they enjoy the craft of making the thing. And like for you and me, that's probably like actually like writing those first few lines of code, like having those first few customer conversations, like getting that first MVP into someone's hand. You're like, you're there and you're like actively doing the work. And there's something that's so satisfying about that. Now, the problem is like when you're CEO of a multi-hundred or multi-thousand person company, your job is rarely Do the work. Your job is like build the organization capable of doing the work and hire and retain the best people and like give them good career trajectories and all that stuff. And like that is interesting work, but it's different work. Like I don't write any code these days and like I kind of miss that. I'm not on tons of customer calls these days. I'm on a fair bit because as we just talked about, I like to stay super close to it, but not nearly as many as I was in the early days. In the early days, I sold the first hundred accounts myself. Like I was on the phones all the time. And so I think it's important to introspect on what actually brings you joy and how do you make sure that the way you're spending your time mostly involves that. And I think there is an alternate reality where actually, and this is related to not raising a VC, there's an alternate reality where you bootstrap the thing, you keep it super small, and you're laser focused on the actual doing of the work because that's what brings you joy. That's the claim of this tweet. It's like, if there was an alternate universe where I was not doing what I'm doing now, and to be clear, I really like what I'm doing now, the alternate universe is that. It's not trade pilot to do a startup for that is shaped like pilot. It would be trade pilot to be a hacker again.
Andy M:
It's like to be in a room with the engineers writing the code. There's a beauty to that. There really is. There's such a beauty to to like sitting down and doing the work, right? And like builders like it, you know, and it's kind of a curse sometimes because sometimes as you mentioned, this is the problem I have. I always think I can do everything, right? And I know though, like, you know, my wife's great at telling us like, hey, you know, you can do that, but you probably shouldn't because you got to focus on the sale right now. Like, you know, you could get in there and build this thing because you know, it needs to get done. But don't do it. Let the team do it. And you focus on the sales. And I'm like, shit, you're so right. So my question to you is, when did you flip the switch? Right. Of like, okay. And maybe it was gradual. I don't know. But when did you flip the switch where it's like, okay, I'm doing everything I can right now too. Okay. Now I'm backing up and I'm going to, my focus is recruiting and putting people to do the things like, when was that? Totally.
Waseem Daher:
And one clarification, which is, look, we talked about this in the context of like writing the code or whatever, but it's equally true for the seller. Like you're going to be tempted to just like, well, again, let me just like sell the next a hundred accounts. Cause I'm like good at it and I'm passionate about it. And customers like talking to whatever. But actually, no, the work to scale is like, okay, how do I build the sales at work? And again, that's very different work than the work of doing the selling. So I think it almost doesn't even, for the builder or the seller, I think this dilemma in some ways is, it's true for both. Now, to your question is like, when do you shift gears? Well, I think for me, it's probably about like, and for me, it was actually, you know, at this company, I was principally on the sales side. Like I didn't write any code of pilot. For me, it was like, okay, do I feel like the sales process is systematic and repeatable enough that I could train someone to do it? And do I feel like I'm a bottleneck on the process? Are we not selling as much because we are not able to give every prospect as much love as they should be getting because we don't have enough staffing working on it? Those are the two things I would look for. It's like, okay, cool. We've got the phone ringing a ton. We're not actually able to, like, give them the love they should be getting because, like, I don't have time to answer all these calls. And we feel like we actually understand how to sell it, who we're trying to sell it to, like, what resonates, et cetera. When those are true, that's a signal to me that, like, oh, okay, yeah, we're overdue actually for having, like, scaled this up a little bit. Like, my job is now build the machine capable of doing it. It's not continue to do it.
Andy M:
Got it. So long story short, it's when you start to feel like you're a bottleneck in the process. And that's when you're like, okay, I'm out. I need to get someone to do it. Because I'm feeling this right now in some scenarios where it's like we're creating templates in the platform and I'm holding up the designer because I need to get back to it. And you feel that and you're like, well, I'm the issue now. I'm the problem, me, I'm the problem. And so it's interesting, and you kind of got to, I feel like get rid of your ego a little bit on that too, right? Because there's like, there's this feeling of like, no one's going to do it as good as I do because this is my baby. Yes. Right?
Waseem Daher:
Yes. Right? And that may be true, by the way, but it almost doesn't matter whether it's true or not. You cannot continue to do it because you're a bottleneck. And even if the person who's going to do it in your stead will do it at 90% the quality you're going to do it, it's still the right decision for the business. But yes, it's hard to let go because you know how to do it, you do it well, and you know what? You like to do things that you do well. And this new thing is a thing you haven't done before maybe, and therefore is a thing that you're probably not going to do very well because you've never done it before. And of course you'd rather work on the thing you're good at. It's much more fun to work on the thing you're good at than the thing you're bad at. But unfortunately, as the company scales, your job is basically continuously doing things you're bad at that are new to you that you haven't mastered. Because if you have mastered them, it's probably time to like hand it off to someone else and like tackle the next even bigger problem for the business.
Andy M:
Yeah. Yeah. OK. I like that. And it's also too, you know, like On another podcast, you mentioned hiring a salesperson and you were like, well, when should we hire a salesperson? People's first instinct is, well, we have the product, let's get someone to go and sell it, right? But there's that issue that can occur of, well, what if this thing's not the right thing we're selling or people aren't going to buy it? Then you have an issue with the salesperson and yourself, and you might do it too early. And this is good feedback that you sold the first hundred accounts, right? And how long did that take you to do, Waseem?
Waseem Daher:
I don't remember, but I feel like I was the sales rep for the first year of the company, at least.
SPEAKER_01:
First year.
Waseem Daher:
And then when we had the first sales hire, this woman named Kate, who was awesome. Like she and I did a bunch of it together. It's not like I was like, cool, over to you. Like, no, it's still like, look, I'm still in the mix. You know, now seven plus years in, I'm like still on sales calls. Like right after this, we're doing a sales, I'm doing a sales call with one of our reps. Um, but it's, you know, it's not like you just like hand it off and you're done. You're still involved. Just hopefully you, you're starting to build a process and a playbook to do the work well at scale.
SPEAKER_01:
Yeah. Yeah.
Andy M:
All right, we'll wrap it up here. I know we had 45 minutes. So a couple of questions I have for you, which is one, people love this question. It's very basic, best business book that everyone should read. What is that?
Waseem Daher:
Well, we're kind of like thinking about sales on this, in this pod. There's a book called Founding Sales by Pete Kazanji. It's actually free online and you can also get it on Amazon or whatever. I actually think it's super good. Like I think it's a, it's so tactical and I think that's what, especially if you're like, if you don't have a sales background and you're a founder, you like want to learn how to do sales. I really, really like Founding Sales.
Andy M:
Yeah. What was more impressive about that book you recommend is how you know how to pronounce Pete's last name. Cause I never know how to do it.
Waseem Daher:
Well, I'm not 100% sure I got it right, but hopefully he'll call me if I got it wrong.
Andy M:
Yeah, PK. Yeah, PK. PK. You know, PK. All right. Best purchase you've made under a hundred bucks recently.
Waseem Daher:
This is like, okay. It's like a little earplug thing. It's called like loop engage or whatever. It's like a silicone earplug. And the idea is that like, they built this thing for like, you're going to a concert. It's like too loud, but you still want to like hear the music. You put this thing in and it just makes the world a little quieter. And I actually like if I'm on public transit or somewhere noisy, just having the world be a tiny bit quieter is surprisingly soothing.
Andy M:
Very interesting.
Waseem Daher:
Looping gauge. Okay. I think that's what it's called. It's just like, you'll find it if you Google that thing. It's basically like a silicone reusable earplug that is like subtle. It looks like, you know, it does not look like you have a big foam earplug in your ear or whatever.
Andy M:
Interesting. Okay. I want to, How did you discover that you said heard on a podcast or something?
Waseem Daher:
What was the this is this is? Maybe embarrassing. I have a three-year-old when he was like much younger all babies cry obviously and you're holding the baby like right here and they're crying directly into your ear and it's super loud and Like, you still want to be able to hear the fact that the baby is crying, but maybe you don't need to hear it at 120 decibels. Like, having a little bit of just, like, sound attenuation, I found, like, decreased my stress, like, by a factor of two. I could just, like, much more easily manage, like, okay, you were crying, let me figure out how to get you to stop crying.
Andy M:
As opposed to, like, when it was at full volume, my brain was like, boop, boop, you know, it's just like... It's like, it reminds me of that situation where you're driving and, like, you have to, like, really drive intensely and you turn the music down. Because you're like, all right, I'm going to be a better driver now. Totally.
Waseem Daher:
I feel like, yeah, your brain, if you can shut off some of the inputs, it lets your brain focus on the other inputs.
Andy M:
Yeah. And you know what's so funny is I have that same story. I have an 18-month-old right now, and I would put in earplugs, right? But they were light ones, and so it wasn't the same one. But my wife would be like, wait, you're not going to wake up and put in earplugs? I'm like, no, I can still hear the baby crying. You'll definitely still wake up. Yeah, I'm definitely still going to wake up, but it's just not going to be like, You know, like it's just going to be, Oh, okay. I'll get up and do the thing and, you know, make you have it. So that's so funny. That is exactly what I did too. Um, but we'll see, this has been great, my friend. Uh, thanks for hopping on. Um, love it. People can find you if they want to, you respond to email. So if y'all have questions on pilot or anything was seen at pilot.com, I think.
Waseem Daher:
Follow me on LinkedIn and follow me on Twitter Yeah, thanks for having me on this is really fun. Glad the glass do it.
Andy M:
Yeah, this is amazing. Thank you, my friend. Thank you. Appreciate it
