Sales and Marketing + How to Talk to Investors with Tyler Bosmeny and YC Partners (HtSaS 2014: 19)

Talking, okay great. Um, so okay great, thanks for having me. So my name is Tyler, I'm the CEO of Clever and what I want to talk today is about sales, and I have a little bit of insight into this.

I graduated college, I actually studied math and statistics probably like some of you here in this room and thought I was destined for this world of finance. I was about to go start at a hedge fund, and at the last second, a friend of mine roped me into joining his startup and asked me to do sales there, which was something that I knew nothing about.

So I had to figure it out on the fly and spent a couple of years there figuring out sales for this very early stage company. Then when it came time to start Clever, you know, we started Clever and I did it with two co-founders who were very technical and one very product-oriented, and we wanted to build this product for schools.

I thought that experience would have no relevancy whatsoever, but it turns out that some of the things that I picked up at this previous job where I was figuring out sales have been huge parts of what's made Clever grow so quickly today.

A quick background on Clever: we build software for schools. We are an app platform used by developers, and it's used today by about one in five schools in America. We started it about two years ago, and so sales has been a key piece of that.

I want to use this time to just share some of the things that have worked for me along the way. Of course, there's a million ways to do this, so you'll find what works for you.

So first, I want to start about how most how I used to perceive sales, and a lot of people see sales as having this, you know, a lot of mystique around it. You know, it's people who are, you know, really articulate and impossibly charming, and they have these killer closing lines that they use. I think this is how I saw sales, and I think this is how a lot of founders I talk to see sales because they say things to me like, you know, "We're just going to work the product and build a great product and then when it's finally finished, we're going to hire the salespeople."

What I've learned is that hire the salespeople as a founder—the reality is that's you. So, you know, Paul Graham likes to talk about how there's two things you should be doing at any point in time when you're starting your company. You're either talking to your users or you're building your product, and that talking to your users part—that's selling.

So, you know, this is intimidating to some people because they're like, "I've never done sales," and "I wouldn't even know where to begin." But it turns out that as a founder you have some unique advantages that make it possible for you to be really, really good at sales. One of those is your passion for the product and what you're building, and the second is your industry knowledge of what you're—of the industry and the problem that you're solving.

Those two things actually totally trump sales experience from what I've seen. So this is actually my co-founder doing sales. This is what sales looks like, you know, in the very earliest days of a startup. It's not Don Draper; it's a lot of calls like these.

But this is something that even as a founder who's never done it before, it's very easy to do. But you have to commit yourself. What we did at Clever was we dedicated one founder, which was me, to peel off and say, "Okay Tyler, you got to go figure this out and work on this full-time because it's so important to our business."

A couple of things that I've picked up about sales along the way in trying to figure this out, you know, the first thing that everybody knows about sales is they say, "Okay, it's a funnel," and you have these different stages of funnels and of the funnel, and you move your customers through it.

Pretty common categories: there's this prospecting category where you're trying to figure out who's even interested; then you're having a lot of conversations, which is a second level of the funnel; then you're finding out who's really serious and you want to close them and sign the deal. Of course, you're in the promised land of revenue.

What I thought would be interesting would be to talk about each stage and a couple of strategies that we've used at Clever that have worked really well so that these aren't abstract things but things that, you know, you can hopefully use at your startup.

So, prospecting. Prospecting is the process of figuring out who will even take your call. One of the things that I realized early on—there's this guy Everett Rogers who created this technology life cycle adoption curve, and he describes it as a bell curve where you've got, you know, your innovators who will try new things and you've got your early adopters, your mid-stage adopters, your late adopters, your laggards.

One of the things that was really helpful for me in understanding sales at an early startup is he's quantified the tail of this bell curve. This part over here, the innovators, those are your potential customers. It might seem discouraging that only 2.5% of companies are your potential customers or would even consider buying from a startup that has no users and no revenue, but actually, I found just the opposite.

I found it to be extremely helpful to have this frame of mind because you realize when only 2.5% of companies will even take your call or consider using your product, you realize what a numbers game this becomes. So if you want to reach that 2.5% and you want to get some early sales, if you're starting to do the math, you're hopefully starting to realize you have to do a lot of calling. You have to talk to a lot of people.

So early on, in the early days of Clever, this was my job. In the first two months of YC, I reached out to over 400 companies trying to get them to take a call and talk to us about what we were building.

There are three ways that I have found most successful in prospecting and getting these people: one is your personal network, that's obvious; I'm not going to spend any time there. Another one is conferences, which is surprising to a lot of people; and then the one that people are most familiar with is cold email.

When I say conferences, this is what people think; they think I'm talking about CES or, you know, E3 or something. Actually, the kind of conferences where sales happen look more like this. We would, in the early days, go to a lot of these because you've got to go to where your users are. If you're selling to CIOs and there happens to be a gathering of them at a hotel in Milwaukee, guess what, that's probably where you should be.

So we go to conferences like these. We'd get the attendee list in advance, we'd email every single person in advance and try and set up meetings so that when we get there, every single minute of that trip was well spent. This was huge in Clever's early days; this is where we met all of our earliest customers.

The second thing I mentioned is cold email. A lot of people don't know how to write cold emails. It's actually really easy, and the key is not to write a lot; it should be really concise. This is an email template that I used early on and you're welcome to copy it, but it's really short: here's who I am, here's what I'm building, and I'd love to talk to you about this. Could we find time tomorrow?

It's really easy, and you can customize this and find out for every business you want to sell to who's the right person to send it to, and you can send out quite a few of these.

So alright, that's prospecting, and the reason this is so important is because you've got to build that first layer of the funnel. Then you get them to take your call and this is another place where a lot of founders I think just have a lot of questions about what to actually do. The biggest thing to take away—in fact, if you only take away one thing from this presentation today—the number one thing you should remember is when you get them on the phone, remember to shut up.

That's really surprising to people. So many founders when I help them with their first sales pitch, they finally get somebody on the phone who wants to talk to them about their product, and they're so proud of this thing they've been building for the last three months that all they want to do is get on the phone and talk about every feature and talk about all the different things it can do and talk about why it's the greatest thing in the world.

I have that temptation too; it's just part of being really proud of something. But it turns out that if you watch the best salespeople, like the best salespeople in the world, the top 1%, and you have a chance to listen in on a call with some of those people, like I have, the most surprising thing is how little talking they do. In fact, I've seen calls where the salesperson told me their goal was to only spend 30% of the call talking and have 70% of the call be the other person.

They would ask a lot of questions and say things like, "Why did you even agree to take my call today? This problem that we're talking about solving for you—how do you solve it today? You know, what would your ideal solution look like?" They're not doing the talking; they're finding—they're doing everything they can to find out what this person needs and hopefully understand their problem even better than they do.

That's what really great sales is. In fact, this is something I drill into everybody at Clever; it's a really important part of sales. And there's actually—now, if any of you use Uber Conference, they have this amazing feature where when you hang up a call, it sends you an email automatically and tells you how much you talked versus how much the other person talked. Looking at one of those emails, you know, if someone doing sales at Clever, I get one of those emails, I can tell immediately how likely the sale is based on how much talking we were doing.

So you got these people, now you got on the phone, do a lot of listening, really understand their problem. The other part of this stage that surprises a lot of people is follow-up.

So here's a lot of different steps that you can imagine going through, you know, emailing somebody, not getting a response and emailing them back, calling them, leaving a voicemail, having a pricing call. You know, there's probably like 60 things up here on this slide that could be steps for closing a deal. These actually aren't just random things; this is one deal. This was the second deal Clever ever signed. These are all the different steps that we had in order to get this done, and you can see there's a lot of really embarrassing things up there like I emailed somebody and they didn't respond, and I emailed them again, and they didn't respond, and then I emailed them again.

This is from somebody who wanted to buy our product. Isn't that crazy? This surprises a lot of people. I see so many founders who they have a great call with someone, they send an email, they don't hear back, and they say, "Oh that person might not be interested."

Well guess what, this is what it looks like in the best case. And so you really have to have kind of this unhuman, unreasonable willingness to follow up and drive things to closure. Now, I'll qualify that with one thing which is to say, when you're starting a company, your time is extremely valuable because it's your only resource, and you couldn't possibly do this for every single person who might buy your product.

So your goal should be to get people to a yes or a no as quickly as you can. Where you die is if you have a thousand maybes, and sometimes I talk to founders who say, "Oh yeah, I have this great pipeline of, you know, a hundred people who have expressed interest in our product," and the maybes are what kill you. If you can get to a yes or a no, in some ways a no is even better than a maybe because it allows you to move on and focus on somebody who might be a yes.

So have this superhuman level of follow-up and ambition, but make sure you're focusing it on the right pieces. Alright, so you've talked to some—you've talked to a ton of people, you've had all these phone calls, you've followed up with them ridiculously to the point where they just know you're not going away and they’ve got to sign an agreement.

This final step is something that if you haven't done before might seem opaque, but it's actually really simple. It's called redlining. So you'll send over an agreement, their lawyers will mark it up, your lawyers will mark it up, and you kind of go back and forth.

If you're part of YC, this is really easy because YC has standard template agreements that they give you so you don't have to find these, and you can just, you know, use those. But if you've never been involved, you kind of had to figure this out on your own.

One of the things that I'm really excited about is as part of this presentation, YC has agreed to open-source their deal documents. So these documents that YC founders used to get are now going to be available to everybody, so this should hopefully never be a barrier to anyone who wants to do sales for their startup. You've got some great documents.

Then the other thing I'll say about this, a place I see so many smart people go wrong is you got to remember what your goal is: your goal is to sign some deals and get some reference customers and get some validation and get some revenue. If you don't do that, your startup is, you know, toast.

So in light of that, it's really surprising how many smart people will want to do ten rounds of document review, quibbling over the most minor points because of pride, because of intelligence, whatever. You know, make sure the agreement is the way you want it, but then sign it and move on.

I've seen founders spend months quibbling over some indemnification clauses and their business would have been way better off if they'd, you know, just signed the deal and moved on to the next one. So that's one closing trap you can fall into.

I have two more. One other closing trap that I see founders struggle with a lot is they're talking to a company who says, "I will use your product, but I just need one more feature," you know, or they say, "I'd love to use your product but it doesn't have this one feature so we're just not ready."

To most people, especially if you're ambitious, when somebody says that to you, what you want to hear is, "Oh, well I can build that feature, great! You know, I'll build that feature, and then they're going to use my product." But the problem is it almost never works that way. In fact, somebody telling you that they want to use your product but it's just missing this one feature, I would almost map that to a pass in your mind.

Because nine times out of ten, if you actually built that feature, you go back to them and then there'd be one more feature or there'd be some other reason that they're not using the product. So if somebody says to you, "Hey, I want to, but you know there's this one thing that's preventing us from using your product," I would do one of two things: one, say, "Well, that's great, let's sign an agreement and we will put in the agreement that we're going to build this feature," in which case you know that if you build it, you're off to the races.

Or more commonly, what we did at Clever was we would say, "That's great, we're going to wait to see if we hear that demand for more customers." And then once you have a lot of customers requesting it, then you should build it regardless, and then you're not—you don't have to worry about doing something that's customer one-off, which is what you really want to avoid.

So don't fall into this trap; it happens all the time. The other trap I would highly, highly recommend you try to avoid is the free trial trap. This happens all the time. People, you know, they go down this path with a customer, it seems really exciting, and then the customer says, "Oh, well can I get a free trial?"

You can't blame them; that's a totally reasonable thing to ask for. But the problem is when you're starting a startup you need revenue, you need validation, you need users, you need commitment, and free trials get you none of those things. So you go, you do all this work, and if you end up with a free trial, unfortunately, you haven't made as much progress as you—you think you've made progress, but really at the end of the free trial, you're going to have to sell them all over again.

The way I handle this that has worked really well is when somebody says, "Can I get a free trial?" you say, "Well, we don't do free trials, but what we can do is we do annual agreements here, and what we'll do is for the first 30 or 60 days, if for any reason you're not happy, you can opt out."

That's a way to get you the things that you need while giving them the comfort that they might need to take a chance on a startup. So that minor change actually makes a night and day difference when you're thinking about these things.

Alright, so you've prospected, you’ve had a lot of conversations, now you've closed people, you've gone through the redlining process, you worked out the free trials, and you're on your way hopefully to your first sales.

Now early on, you can think of sales as just like any other thing of a startup. Your goal is that you don't have to do things at scale. In fact, you can purposefully do unscalable things to try and get early customers. That's the fun of it. But the other thing that I think is really important to keep in mind is once you've done this enough, what you should start thinking about is what aspects of this are repeatable, and what aspects of this, you know, are we going to scale further.

There is this Christoph Janz who says this really great blog post online about the five ways to build a $100 million company, and he talks about how you can have a thousand customers buy a product that costs $100,000, or you can have 10,000 customers buy a product that costs $10,000, or you can have 100,000 customers buy a product that costs $1,000.

Even though you don't need to know on day one which bucket you're going to fall into, most companies do fall into one of the buckets. So you start thinking about that as you're doing this. If you want to be in the elephant category of a $100,000 product, that's great, and you're going to have a really high-touch sales cycle and that's fine. You know, that's Salesforce, and Workday, that's great. But if you think you're going to be a rabbit and sell products for $1,000 a year to businesses and your sales process involves flying out to see them three times, and eight demos, and you know, three months of redlining, then you probably have to rethink something.

I see a lot of startups most commonly in that who want to be the rabbits and sell for a low-price product to businesses not thinking about how to do it in a scalable way. That's one area where you can get underwater, or it just forces you to increase your prices.

So this is how I think about different businesses and it'll be helpful for you when you get started and once you've done enough of the sales to say, "Okay, you know where am I?" and the correl to that is how do I have to price my product to be a viable business?

So those are some of the things that I figured out along the way building sales at a few different companies, and specifically on this very narrow stage of 0 to 1 million. After you get to 1 million, you’ll find there’s a million blog posts, you know, about how to get from 5 million to 50 million or 10 million to 100 million.

But this zero to one step, I wanted to focus the presentation on that today because there's not as much written about it, and it is something that I think is very opaque to a lot of founders. I figured this out just by doing it, and I'm confident that if you're starting a company, you can too.

If for whatever reason you'd like to do what I did and join a startup that's figured it out and hone your skills and hone your craft, we are hiring at Clever, so that's an option. But even if that doesn't happen, if you want to start your own company and you have questions about sales, I put my email address up here, and feel free to reach out anytime. I'm happy to help.

So thank you; thank you very much. Yeah, that was awesome.

Um, alright, so now we're going to talk about a little bit more detail on how to raise money. Michael is first going to talk about how to see the pitch, and then C will do in role play.

Mind glowing, you know, it really is basic blocking and tackling, but one point we want to make before we get started is we actually don't spend a lot of time at YC focusing on this. The main reason is the best way you can make your pitch better is to improve your company. If you have traction and your product is doing well, these conversations are like the investors want to see you succeed.

And so if you remember anything, it's make your company better, and the pitch will be easier. We're going to spend the time in three sections: before the meeting, which Michael will kind of focus on; we'll do a role play of what meetings actually look like; and then we'll just wrap it up. We are going to do Q&A at the end; we'll kind of say five minutes, so if there's something we don't cover, please write down your questions and we'll go through them.

No, without further ado, beautiful, here.

Alright, so, my name is Michael Syel. I'm a current YC partner. I've started two companies—one was called Justin TV; it ended up selling to Amazon. The other was called Social Cam, which sold to Autodesk, and what I really wanted to do was break down and demystify the process of creating a pitch.

So I think what happens too often when I see companies come to talk to me is that they don't know how to simply explain what they do and then ask for money, and that's basically what you have to do as a founder. So we're going to go over four things: the first is what your 30-second pitch is. You need to be armed with this constantly; this is basically how you talk about your company. This is magic.

Whether you're talking to people who want to give you money, who don't want to give you money, you're talking to your parents, this is your go-to. The second is your two-minute pitch. This is for people who are more interested—this is people who you might want to raise money from, or people who you might want to get to work for you, or people you actually kind of need to get a little bit deeper.

Notice that's where I stop. A lot of people practice 10, 30-minute pitches, hour pitches; I think that's all garbage. I think you can get everything you need done in 2 minutes, and one thing I like to tell founders is the more you talk, the more your opportunity to say something that people don't like, so just talk less, and it'll probably be better.

Then I want to tell you about when to fundraise. I think a lot of companies get this a little bit wrong. And then quickly how to set up investor meetings.

So, 30-second pitch: this is so simple, it's three sentences. You can take your time, you can breathe when you do this. You don't have to get that much information out. The first is one sentence on what does your company do. Everyone I meet for the first time screws this up; you have to be able to do it in a way that is simple and straightforward that requires no pre-information on my part. You have to assume I know nothing—literally nothing about anything.

This is how you make it super simple. So, you know, usually what we tell people is apply the mom test. If in one sentence you cannot tell your mom what you do, then rework the sentence. There is a one-sentence explanation that your mom or your dad is going to understand. So really, really start there, and it's okay if you use really basic language.

It's okay if you're saying, "Hey, we're Airbnb and we allow you to rent out the extra room in your house." That's simple, right? You don't have to say, "We're Airbnb, and we're a marketplace for space." I don't know what that is; that's going to require more time.

So use simple language; very important. The second is, how big is your market? It makes sense to do a couple hours of research to figure out what general industry product is in and figure out how big it is. Investors like to hear that you're in a multi-billion dollar market; it's pretty simple to do this.

You know, Airbnb might say, "How big is the hotel market? How big is the vacation rental market? How big is the online hotel booking market?" These are simple numbers to look up on Google, and it makes an investor understand, "Oh wait, if we really blow this company up, it can be worth billions of dollars."

Don't skip this. The second sentence: how big is your market? Third sentence: how much traction do you have? Ideally, this sentence is saying something on the order of, "We launched in January and we're growing 30% month over month. We have this number of sales, this amount of revenue, this number of users." Very simple.

If you can't speak to traction in terms of pre-launch, you need to convince the investor that you're moving extremely quickly. So the team started working in January; by March we launched a beta; by April we launched our product. Convince the investors that you guys are moving fast—that this isn't some long slog, that you guys aren't thinking about this like a big corporation; you're thinking about it like a startup where you can move fast and make mistakes.

That's all you have to do in 30 seconds: three sentences. From that basis, you should be able to start a conversation about your company. From that basis, I understand exactly what you do. You have no idea how valuable it is to be able to explain to someone what you do in 30 seconds, so really internalize that.

If you take nothing else away, that's gonna help you. Okay, two-minute pitch. Now you've got someone who you actually have to convince of something—maybe even someone you have to ask for money. So I like to add four additional components, and these also go by very quickly.

The first is unique insight. Now, if you talk to VCs, they'll say stuff like, "What's your secret sauce? What's your competitive advantage? What's your unique insight?" It's all the same thing. When I think about unique insight, what I think about is here's your opportunity to tell me something that I don't know. Here's your opportunity to tell me something that the biggest players in the market you're trying to enter don't understand or don't do well.

This is the "aha" moment, and you better have it down in two sentences—the "aha" moment. So you got to crystallize all of the reasons why you guys are going to kill the competitors or the really intelligent thought that got this business started in two sentences. I need to "aha" you. You can see whether it's happening when you're saying it; that's why I like two sentences, so you get in and out fast.

So if I look at you and I'm like, "Huh," then it's okay; you nailed it. If I look at you and I'm like, "I already knew that," then you didn't nail it. If I look at you and I just don't understand what you're talking about, you definitely didn't nail it. So practice that unique insight in your two-minute pitch; that's all you're only going to get two sentences to get that out there, so it can't be complicated.

And that's basically the theme of this whole thing, right? It cannot be complicated. Next, how do you make money? You know, your business model. I see so many founders run away from this question because they think things like if I say advertising, people are going to be like, "Oh, that's stupid!"

Just say it! Don't run away. If it's advertising, say advertising. Facebook's a massive advertising business; so is Google. If it's direct sales, it's direct sales. If it's, you know, a game and you're selling in-app add-ons, like that's fine, just say it! Don't run away from this sentence.

It only has to be one sentence long. Where founders get tricked on how you will make money is they say, "Well, we're gonna run advertising—maybe some virtual goods, we're going to figure out how to do this and maybe this and maybe this." Well, now you're saying nothing!

Now you've told me you have no idea how you want to monetize this. This was a check mark that I just wanted to write down—they know how they're going to monetize! Instead, I'm writing a big question mark. So do the thing that everyone else in your industry does to monetize. 95% of the time, say it and move on like it’s totally okay!

No one's going to hold your feet to the fire and say three years later you didn't monetize this way, but it's much better to be clear and concise than it is to start spouting out every single way your company can make money.

The next one is team. I think that this answer is actually really clear. I think you're trying to do two things: if your team has done something particularly impressive, you need to call that out. We were the founders of PayPal? You want to say that.

We were the founders of Amazon? You probably want to say that. So if you guys have done something that has made investors money, you want to say that. If not, then please don't go on about the awards your team has won or the PhDs, or I don't care.

I don't care what we want to hear is how many founders—hopefully between two and four—we want to hear how many of them are technical, how many engineers versus business people. Hopefully, it's 50/50 or more engineers. We want to hear is that how long have you guys known each other? We don't want to hear you guys met at a founders' dating event three days ago.

Ideally, you've known each other either personally and professionally for at least six months. We want to hear is that you're all working full-time, it's really helpful, we are all committed to this business, and what we want to hear is how you met.

That's it! You can get in and out of that in two sentences; very easy. Your only way to build credentials is if you've accomplished something, and with an investor, typically it's if you've accomplished something that's made someone money.

So don't try to overinflate yourself; if you don't have that stat on your résumé, move on! The more you talk about a bad thing, the worse it looks.

So the last one is the big ask. When it comes to this, you have to figure out whether this is a conversation that involves fundraising or not. What I tell people is like this is the time where you kind of have to know what you're talking about. This is a time where you have to know are you raising on a convertible note? Are you raising on a SAFE?

You have to know what the cap of that SAFE is. You have to know how much money you're raising. You have to know what the minimum check size is. These are things where if you don't know these things, investors are going to be like, "Oh, these guys aren't serious," or "They haven't done their homework!"

So whereas in the rest of this whole thing, you shouldn't use any jargon; in this part, you shouldn't just be like, "Oh, we're just raising some money," like now is the time to actually use a little bit of that jargon. If you don't know that jargon, Google-search it! It's real simple; you guys learn it fast.

So that's it, by the way; that's your pitch done. Like, game over. Now you let them talk.

So, when to fundraise: I think this is so important, right? You've got this little growth graph here. Investors like to invest based on traction, and so literally it's always better to raise money when you've got more traction than less.

Oftentimes, though, you guys will be in a situation where you're just starting, or maybe you just launched. So what you need to do is you need to think about how do you flip the equation? Your entire mindset should be typically you are the ones asking investors for money and therefore they are strong and you’re weak.

How do you create a scenario where you are strong and they are weak? Right, that's where you want to be fundraising. So first, how do you know that you're strong? If investors are asking you to give you money, you're strong—that might be a good time to start fundraising.

If investors aren't asking, are you talking to people about your startup or are you running super stealth? If you're talking to people about your startup and you're getting the word out, either that’s through the press or just through talking to your friends or people you know doing startups, that's a good way to kind of start feeding that.

The second thing is, have you created a plan so that you can launch and grow without needing to raise a bunch of money? 95% of the startups that I meet can get a product to market with a very, very little bit of money.

So never put the investor in the ultimate position of power: "We can't do anything until you give us money." You always want to flip it around. You always want it to be—this thing's moving: we all left our jobs, we're all working full-time, and it's moving.

If you want to jump on, great; if not, there are a lot of angel investors. That's the attitude you want to have, that's the confidence you want to have. If you need money early, always plan for needing less money and always, always be able to show that you've got a fully committed team that's working fast.

That's going to be how you gain an advantage when you can't show traction. If you can show that investor that you haven't launched yet, but you've done eight months of work in one month or two months and you've got a great team that have all quit their jobs and they're totally committed, you get some of that advantage back.

But you don't get all of the advantage unless you're launched and growing, so something to keep in mind. Finally, how to set up investor meetings.

This is really, really simple, but I'm surprised at how many companies don't get this right. The first is you want a warm introduction from another entrepreneur preferably or a previous investor of yours; that's where you want to start. If someone who's passed on your company as an investor offers you to make introductions, that's kryptonite; don't touch that.

So first, warm introduction—very simple. You don't want to cold call these people; you don't want to bum rush these people. The person—the credibility of the person who's introducing you to an investor is a big part of whether the investor will take that meeting.

Second, think in parallel. So many people that I meet will run the fundraising as a super slow process. We met with one guy this week, we're going to schedule a meeting with another guy next week, another guy three weeks from now. When you're fundraising, you're on—it’s a sprint; it's not a marathon.

So you want to schedule all of your meetings during the same week. It's extremely hard to do, but here's one trick that I love: tell when you're emailing investors, you're getting those warm intros, the investors email you back, you say, "Hey, we love to stop a meeting, but we're building like crazy for the next two weeks, so can we set it up in that third week?"

Right? So then you've emailed everyone that, right? So everyone schedules that meeting three weeks out. It's better for them because their calendars are open; it's better for you because you've got all your meetings in one week.

And also, what did you do? You hinted, "Hey, I'm not desperate for the money; we're building! Like, I can meet you in three weeks, but we're busy." Like it's signaling all of the right things.

So that's the best way to kind of go about how you're going to do that. The last thing is one team member should be invested in fundraising full-time. It shouldn't be something that takes over the whole company because it's very, very distracting.

So with that, let's kick it off to the next part of this. Who am I handing it to? Big Dalton? Yeah, Mike. Oh, beautiful. Hi!

Um, so my name is Dalton Caldwell. I'm one of the partners at YC, and one of the things that we're going to do today real quick is a mock pitch.

First of all, I know this is a bit contrived, but this is in this format of a college class. We're going to do our best to have fun and kind of demonstrate what it's like, and I realized there's a million reasons why this—why you could say, "Oh, this isn't realistic of what pitches are really like," but, you know, again, there's a lot that we can show you just in terms of my background.

Over my career, I've raised $85 million over several companies, so I've sat in a lot of investor meetings, and so I'm going to be pulling as many things as I can. So again, we're just going to try to show you something to talk to and use it as a learning session.

And you already did your intro earlier, Caster, right? Yeah, I mean I've done a couple startups.

So we're going to do two pitches and we're going to go through them pretty fast. As Michael said, these tend to go fast—so let's dive into the first one.

Okay, so, Caster, I understand you're coming to pitch me today. Can what can you tell me about what you do?

Uh, so we're building a communication platform that will allow, you know, businesses and consumers to collaborate on one single platform rather than the kind of fractured state that they're in right now.

I don't know. I don't follow.

So like think about like what WhatsApp or SnapChat does for consumers. We want to do that for businesses.

Um, and what the—I have to do this with a straight face—what that means is we want to enable consumers to talk to businesses. That's really what the goal of our business of our startup is.

I still don't—so who uses this? What does the product do?

Um, so I mean it is for consumers and businesses; it's a messaging product. It allows consumers to—why would a consumer want to use your product? Because they want to message the business.

Okay, well, okay, can you tell me about the market or what the opportunity is? What's the size of this?

How do this—messaging companies are very big. Obviously, WhatsApp sold for like $19 billion, and Snapchat is really growing very quickly as well.

Um, so we—I mean we think the opportunity is very big.

Okay, so okay, okay. Can you tell me a little bit about your traction, your numbers? Like, have you given this to people yet?

Uh, yeah, I mean we don't want to kind of open the koto and kind of go into all the details here. Kind of at a high level, we're live; we definitely have thousands of users in the Bay Area—hundreds of businesses.

Can you tell me who some of those businesses are?

Um, they're ones that you've been to. We don't really want to get too much into the details because, you know, we're still early and we don't want—you know, we're trying to stay stealth.

Okay, well can you tell me about what you've learned so far? What insights that you've had from the consumers—are sending messages to these businesses?

And we think that's great.

Um, so these businesses are responding to the messages, and we think that's, you know, I don't think that's obvious that that would happen.

So can you tell me about what your business model is?

Yeah, so we charge businesses like a monthly rate. We haven't precisely figured out what that is. We've right now—we're free for the, you know, few hundred companies we're in right now, but we're looking to probably do a monthly.

How much do you think a business would be willing to pay?

Um, we think certainly $10,000 to $15,000 a month.

Okay, um, so so anyway, could you tell me a little about your team and who you have working on this?

Uh, yeah, there's—we have five founders. Technically, I'm the only one who's full-time right now. We're raising money so we can get, you know, the rest of the team, uh on board.

Uh, yeah, that's just—or can any other founders, program or?

Uh, yeah, yeah! I mean we have—I mean one of them is a bio PhD, but he's really picked up coding.

The—the—I mean, I'm a Python developer. I did learn Python the hard way.

Look at the time!

Well, it's been really great meeting you! Please keep me in the loop. This sounds fantastic!

I will send you updates! I'll send you—I’ll send you an update!

Great!

Okay, that was awful.

Alright, that was aw. Okay, um, so let's just go through. So that was obviously not strong, so let’s just talk about some of the mistakes.

So first of all, you need to make sure the person you're talking to knows what you do. This seems really simple, but this seems—simple, but it's not. So many times, people get flustered, they get nervous and they start talking really fast, and there's no way you're ever going to convince anyone of anything if they don't know even what your app actually is.

You have to know your numbers. Obviously, if you're very vague or evasive, like don't even have the meeting. If you don't feel comfortable telling an investor what your numbers are, don't even meet with them; it means you're not ready yet, right?

For market size, try to give some plausible bottom-up analysis and don't just name-drop big companies that aren't even really related to what you're doing.

People tend to do that a lot. Try to have insights; try to convince me that there’s something that I don't already know about the market that I learn talking to you rather than just what everyone knows about what the market is.

Right? I learned nothing during that particular pitch.

Also, the team—just like why are you working on this? Why are you suited for it? It's a good thing to do, and finally, like he didn't drive the conversation anywhere; like obviously that went poorly and he just let the conversation just like flail around until I cut the meeting because we ran out of time— as fast as I could.

So anyway, that was not a good pitch.

So let's try that again?

Okay! Alright, let's do this!

Okay, alright Caster! Well, um, so I understand you have a company and can you just tell me a little bit of what you guys do?

Yes, so we're a messaging product. We allow—I mean that sounds kind of vague. So what we allowed you to do is essentially message a location. So when you walk into a Crate and Barrel, you can send the Crate and Barrel manager a message like, "Hey, there's puke in the hallway," or if you’re at the airport, "I'm trying to find this specific gate. I'm not at this airport; where's—where's the terminal for Virgin?"

Or if you're at Target, what aisle is—?

Okay, so is this a mobile app or what?

Yeah, so on the consumer side, we have an iOS, Android app, but really getting consumers to download apps is obviously very—yeah!

I don't usually just download apps to send messages.

Most businesses, we have a call to action which says, "Text the owner directly."

We've tested actually a bunch of copy that works the best; in small print, we have the messages are anonymous. That also lowers the barrier to entry.

I think the most counterintuitive thing we've learned in the kind of launch that we've had—we’re in 350 locations in the Bay. We've been doing this for about three months; we’re about 11% weekly growth rate in terms of acquiring businesses.

But the most constitutive thing that we learned, because we weren't actually sure, is will people send messages when they walk into—do people send what? What’s the number one type of message that people send?

So you would—so originally we started this product off thinking this is going to be like in location feedback—that was the premise—in location feedback. What we found is more than half the messages are actually not about feedback at all; they ask things like we were in this location in San Jose—this Kebab stand, father and son—it’s just a takeout place, and we saw a message that went through that said, “Are you hiring?”

And that’s like very strange because you would think, "Why would you just ask the owner?" But we realize that we know this is the owner and the person who's walking in doesn't. And so they do prefer to actually just text the owner because they think that's easy.

Okay, so it's like a suggestion box or it's like a way to just like message—initially, that’s what we thought what it was, but what we actually discovered is a vast majority of the me—I shouldn't say vast majority—over half the messages are actually just things like when do you open, when do you close?

Because that's not on Google!

Do you have any reservations available tonight?

Okay, okay. Well, look, in terms of your traction, it sounds like you said you had some businesses. Like tell me about what you guys have right now?

So with 350 businesses, all from San Jose to San Francisco, we sold them ourselves as three founders. We are all technical, but we actually did all the sales because we learned a lot about how these businesses work.

We actually come from a retail background. We originally built this product for large enterprise players like Starbucks and Walmart, but we recognized that closing those contracts and our limited amount of runway wouldn't really be possible.

So we wanted to get the product in the hands of users, so we did SMBs and that's when we discovered, "Hey, this messaging product that sounds interesting."

It sounds like you have some customers. I mean, this could be big, though.

Okay, maybe you can get in terms of like numbers. We see one and a half messages on average per location per day. That might not sound a lot, but for a business that's getting 30 messages, you take like a Yelp review or Google review.

In a lifetime of business, they might get five or seven, so they're getting a huge volume of messages relative to what they tend to experience, and they're private, so they're not public.

So in terms of how do we actually make money, it's not—you know, frankly speaking, we don't have a very clear answer there; the two paths are the SMB side or the LCS side, the large customer side.

Large customers, we know from our retail experience, just regular feedback tools are $3 to $4 million per year; it’s like a Sears where we came from. SMBs—we've tested—are willing to pay $50 a month.

So I certainly think this can be a large business, but I could see that just a couple things like can you tell me about your distribution strategy and also just a little bit about the team?

Yeah, so distribution—so the thing that we learned in selling these SMBs is it's really freaking hard.

The formula: LTV minus CPA—lifetime value minus cost-per-acquisition—SMB is never going to work out. So we have two solutions: one is to go up-market like originally planned to Starbucks or Walmarts, or two is actually pair with consumer-facing companies: Yelp, Google, Facebook.

Have you been talking to them?

They want to do it, so we've talked to Google and Facebook; we're meeting with Yelp, but we basically want to do is every time you search for a business, there should be a message button. We want to get consumers in the habit of knowing they can send essentially a text message to any business.

That can help us get broad distribution. Our real vision is to become the infrastructure—the messaging infrastructure—between consumers and businesses.

If that doesn't work, let's say Google, Facebook, and Yelp don't want to give up that valuable property; it's really an ad unit.

Okay, um, we do want to just sell this as a feedback tool to large players.

Alright, can you tell me a little about the team? We're running low on time.

Yeah, there's three of us—all technical. Mike and I did a company before; Sunny is an ex-Google engineer. We come from retail, and our first startup was a failure. So I don't know if that's good or bad, but we've worked together and, yeah, we're all technical, we've built everything ourselves, and we sold everything ourselves.

Okay, um, so we've already had a couple of conversations with your firm. We're raising $500,000 and an $8.5 million convertible note. Of that $500,000, $250 is committed by Mike Maples, Elot Gil, and Aen Sink, and Mike with Floodgate is willing to fill around. We think you—and your firm—can bring a lot to the team with your retail experience.

Is this something that’s interesting to you?

Yeah, you know, I think this is really interesting. I would need to talk to a couple more folks on my side, but I do think this could be pretty big.

Yeah, since we've had a couple conversations before, and we’re certainly willing to meet again, we are closing around this Friday.

And so certainly take time and let your other partners know. I'll be available between now and Friday. I'll give you another call before Friday before we close the round, but we’d love to see you in the round.

Okay, well sounds good! I got to go, but thanks for that!

Thanks.

Okay, alright, um, so, very different type of conversation.

Yeah, so do you have the clip?

So in terms of that one, you know, some key points here is try to actually tell a narrative that makes sense to people. You noticed there was narratives; there was talking about people how they really use it—we’re able to tie it down to the real world, which is good.

He was able to demonstrate insights and actually tell me something I didn't already know about the market. There were some tidbits there; it was more collaborative—the meeting felt more like a conversation than just like I was interviewing him about something, in my opinion.

He actually asked for money, and this is the other key thing: at the end, you saw, I could have easily just been like, "Okay, I gotta go!"

But he did talk about fundraising, as Michael mentioned, and he was able to provide all the context and all the questions I would need to actually have a serious conversation with him if he was KG about it or shy about it, and not clear on the numbers.

There's a very good chance that, you know, I probably would have just ended the conversation due to time pressure.

Um, yeah, it's interesting; we sit on the other side a lot. You really—can tell when people are very passionate and know their business very, very well, and that's what you have to become.

Okay, so closing thoughts here before we—we're running a little short on time. After the meeting, the first thing, just like Tyler said in the sales things, follow up. This is important.

And anything other than a check or wired funds is a no! So if they say, "We got to keep talking to partners," I assume that's a no.

And so you do want to put some pressure. The way that you can do that is get deal heat—a deal heat is just a term which means there's a demand for you to be in your round. This is the easiest way and an important way to actually drive a price, etc.

Due diligence on the investor: so let's say you have that $500,000 raise for your seed round on the $8.5 million, like we use this example. Do due diligence on investors.

If you do find out, you know, I do diligence on Dalton, and I find, "Hey, he's actually not a great investor!" I can get Elot or Mike Maples or whoever to actually fill the rest of the round.

It's surprising to us how many entrepreneurs don't do this! You would—it's like you would actually spend a lot of time hiring somebody. You're selling a part of your company to somebody; you should know who you're selling it to to make sure they’re the type of people you think they are.

And then, last, know when to stop. So some founders get so good at fundraising they just want to do it all the time because it’s much easier to do than actually building the company.

You think you could—fundraising does not equal success, and just because you fundraised does not mean you succeeded, and nobody realizes that.

We say this and we'll say this now, but I'm sure everyone will still equate fundraising with success and read about someone's fundraising and assume that means they're successful.

My guess is—my intuition is why this is the case is because a lot of smart people their whole life, they've applied to good schools and applied to good jobs, and they just think fundraising is another application that they can just kind of check off, but building a company is much more ambiguous.

But anyway, that's the session. I don't know if we have time for—oh, just underlining that, build your company. Fundraising is not the goal.

You guys just stick around for a few minutes after and answer questions.

Sure! Yeah, we can do that.

Alright, thank you guys very much; that was great.