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Kevin Callahan: you're the first time founder, you're like, all I see is the 75 million dollars. It seems super simple. I'm a loser. And the answer is no, you're not a loser. things that I would say is like, hey, there's unlimited pre seed VCs. There are tens of thousands of them. You will run out of days before you run out of like VCs. So as long as you are fire and committed and have your process, you will raise money. It's just a matter of how hard you're willing to work for it.
Hunter Harris: Right. Hey everybody and welcome to Build and Breakthrough. I'm your host Hunter Harris. With me today is Kevin Callahan. He is the CEO and co founder of Hopscotch. Kevin, do you wanna introduce yourself a little bit?
Kevin Callahan: Absolutely. well first off, thanks for having me. I'm excited to be here. as you mentioned I'm the CO co founder of Hopscotch and I've worked at a couple of different big tech companies that I'm sure we're gonna get into and I split my t time between San Francisco and Toronto, Canada.
Hunter Harris: I am jealous. That sounds lovely. Do you do the whole what is it? Snowbirding thing? So California during the winter and Toronto during the summer?
Kevin Callahan: Yeah, so the truth is we were one hundred percent in San Francisco, then we had a baby, she just turned two, and now we kind of go back and forth and yeah, we generally spend the winters where it's nice and the summers where it's also nice.
Hunter Harris: Love it. Incredible. Well, jumping into it, so looking over your history, you had pretty lengthy tenure at Twitter, kind of at I want to say what feels at this point kind of like at the apex of our current, like, I don't know, Fang Mang, whatever the acronym is these days, but like Big tech is so heavily mythologized. And I feel that big tech is also really due to the mythologization, is that a word? due to the mythology, a lot of people have a really unusual and distorted views of big tech and what it's really like. So can you speak to a little bit about your experiences with big tech and what it really was like? I don't know, boots on the ground exactly, but what did you experience? What was it like?
Kevin Callahan: Yeah. So I think a few things. One, it's it's interesting that we think of Twitter as big tech, which I guess it is, but when you start talking about Microsoft and Google and Facebook, they all have a hundred thousand, two hundred thousand employees. And so little Twitter, we had like twenty five hundred when I was there. So we had this really big brand, but we had kind of the govern, you know, comparatively small workforce. And so I think on that one particular note it's pretty interesting because because it had a really big brand. you could get into any sort of meeting room or kind of like any room you wanted to around the world. and because there wasn't really, you know, that many people, it's a good shot that, you know, somebody that's really, you know, that's younger, more junior in their career would actually be able to kind of sit in that seat. So yes, it was big tech from like kind of a brand perspective. But yeah, we didn't really have a lot of people comparatively speaking. And I know when you think of You know, even your your average bank, you're gonna have again, like a hundred thousand employees, which is kind of interesting.
Hunter Harris: Tons and tons. So I mean, what was your day-to-day role like in terms of something like Twitter?
Kevin Callahan: So over the course of my tenure, my role kind of evolved and changed multiple times. originally I started off yeah, exactly.
Hunter Harris: As it does, right?
Kevin Callahan: I actually had I I sat down and counted. I think I had like you know ten bosses over the course of my five years, which is pretty pretty crazy. so
Hunter Harris: That's definitely more startuppy than I expect from a a a place like Twitter specifically. So I've definitely had that sort of cadence a few t times myself.
Kevin Callahan: I think in a lot of ways Twitter was more startupy than maybe like the you know traditional big tech. But then again, there was also because of the brand and because of some of that, some of the expectations on the volume of or the importance of the the product, we
Hunter Harris: Exactly.
Kevin Callahan: had other things happening, like okay, you can't necessarily push too fast because If you dox a whole bunch of you know insurgents in the Middle East, they potentially might get killed. Or you you know you have to make sure that you know free speech in certain parts of the world are being adhered to. And then maybe you might want to think about how you are looking about misinformation. And yeah, it was a very interesting place in that regard because yeah, there were some, you know big tech kind of things where maybe we didn't move as fast as we'd like to. But then there was other reasons because you had like, you know, actual lives on the line, which is kind of interesting.
Hunter Harris: Yeah, that that is very d Interesting and different from the sort of experiences that I've had for the most part. Because I'm and I think a lot of the viewership of this podcast, at least the viewership that I'm aware of, is pretty deep in just like your typical B2B SaaS. But man, there's like a whole different world out there of B2C, especially B2C social media apps than Twitter, right? Where there is man, and and Twitter's such an interesting example because Twitter with like the journalism on Twitter, for example, was just like a fascinating I didn't even know what to call it other than just like a fascinating space where so much internet discourse was evolving at this particular moment.
Kevin Callahan: Yeah.
Hunter Harris: so tell me more right like what sort of decisions were you called on to make? What sort of trade-offs were you evaluating here? Like w at at that sort of scale, like How do you go about making, you know, impact and change?
Kevin Callahan: Yeah. I think there's a few things I
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wanted to say as you were talking. I was thinking about it. One thing is that
Hunter Harris: Yeah.
Kevin Callahan: there aren't a lot of brands that people are as passionate about as as
Hunter Harris: That's true.
Kevin Callahan: Twitter specifically. Like people are very or ex ex now. People are were very much like very passionate about it. And yeah, and also like some people just really hated it and really hated the decisions and things that were made. And I think I think back and I think like I don't think people are that passionate about Snapchat or, you know, I don't know, like Pinterest or these other kind of like well, I would almost call like tier two social networks. Obviously you have like the Facebooks that are gigantic and they have bought,
Hunter Harris: Mm-hmm.
Kevin Callahan: you know, the WhatsApps and the Instagrams or whatever. but then you think that the other guys, the other guys are all about the same size in terms of DAU, MAU, things like that, and even revenue. Like everybody was kind
Hunter Harris: Mm-hmm.
Kevin Callahan: of around the five billion revenue mark. And there was n several companies. But yeah, you talk to people over the course of my tenure there and even now, and I say, I worked at Twitter, and then today they'll say, Was it X with Elon? You know, I hate Elon, I love Elon. Like it was it's very passionate.
Hunter Harris: Right.
Kevin Callahan: People would like, I hate Jack Dorsey, I love Jack Dorsey. So it was one of those places that people I for better for felt really passionate about. And and going back to my previous comment around getting into like interesting, you know, meetings. so you know one role that I was kind of brought in to to do or one that I actually found was like how do we do business in China? What does that look like? And you know, one
Hunter Harris: Ooh.
Kevin Callahan: thing we can do is like, actually they are prov you know builders of you know most of the world's cell phones. So you have obviously Huawei and Xiaomi, which people know here, you have Oppo and like all these other you know brands, and they all have different places. And so, you know, hey, can we get preloaded? Like how do we work with them in their browsers? And so first like getting a visa was like super fascinating because it wasn't
Hunter Harris: Mm-hmm.
Kevin Callahan: just I was, you know, Kevin Callahan going to China, it was Kevin Callahan from Twitter, which is you know, state apparatus of the United States government. And so that was like a really fascinating, you know, view where you had to think about security and you had to think about, you know, privacy. but when I you know when we got there and lined up all these meetings, on more than one occasion, like the government was told, hey, these guys from Twitter, this guy from Twitter is here trying to do business with us. and, you know, and an interesting thing, so I'm I'm actually Canadian by birth, and I was meeting the the president of Huawei at the same day as the United the Canadian government was putting I think it was the CFO of Huawei under house arrest and was like arresting her. And so you know being in that meeting room it was
Hunter Harris: I bet that was spicy.
Kevin Callahan: super interesting. It was You know, I'm there and they had all the security, so they had like, you know, three tiers of security. and yeah, it's like, you know, why am I even in this meeting? Like this should definitely be somebody like older and wiser with more gray hair than me. But I think because just the lay of the land I had these opportunities, which is really cool. So yeah. it's a product and a service and a brand that people are very passionate about. And I think that there's just, you know, no place in the world like it.
Hunter Harris: Yeah, and it is interesting that you say that about the brand passion, because even you laying out like the tier one versus the tier two social sites, there's a level of passion that people engage with in Twitter if like comparing Facebook to Twitter, for example, right?
Kevin Callahan: Mm-hmm.
Hunter Harris: People are not passionate about Facebook on nearly that same sort of level. The only the only thing that I can think of that's even remotely similar is how some people relate to something like YouTube and maybe Twitch a little bit.
Kevin Callahan: Yeah. Yeah.
Hunter Harris: But even that is quite different, I wanna say, in part because it's more about engaging with the individual personalities than engaging with the platform, which I think is very interesting.
Kevin Callahan: Yeah.
Hunter Harris: because yeah, I never thought about it that particular way. Do you have any hypotheses for what it is about Twitter specifically that you think kind of like stoked that engagement and that passion?
Kevin Callahan: Yeah. I think like so think of circa twenty fifteen, you would listen to you'd you know, you'd watch the Emmys or you would watch like, you know, a baseball game and they'd be flashing, you know, tweets and hashtags and
Hunter Harris: True.
Kevin Callahan: they would be bringing content from the platform and bringing it in. Even like, you know, whatever, Saturday Live, they'd like Barack Obama and like people coming and reading mean tweets and There was just it was very it was very visceral. It was kind of everywhere. And it was part of the mainstream media. It was part of, you know, culture. and so a lot of people either were so there was you know, we thought of like concentric circles of like how you would like interact with the content on the platform. And
Hunter Harris: Mm-hmm.
Kevin Callahan: you know, you'd have like somebody that's super active and that would be kind of like the middle. And then you'd have people that were You know, they would be less active, but they would still kind of like and retweet. And then you'd have all the way up to people at lurkers and then people that I don't know if you remember, but you you would go on websites, we had embedded
tweets. And so you would go on again, like you'd go on the BBC, or you go on the AP, or you go on like again, ESPN, and they'd have like embedded tweets everywhere. And that showed up, you know,
Hunter Harris: Mm-hmm.
Kevin Callahan: billions and billions and billions and billions of times. So the the product was able to take people's content, like the world's content. And it was also a place for it to live, but it also was a way to kind of help to you know propagate around the world. And so I think people were really exposed to it. And then I think for better or for worse, there were decisions around like who got you know magnified and who got like not magnified. And so I think there was always like that there was like that tension. And also Again, like after twenty sixteen with the Trump win, then I think there was
Hunter Harris: Mm-hmm.
Kevin Callahan: this world around like people deciding like how did that happen? Like what do we miss? And then there's like and there's like you know, Russia this and so anyway, I think it became
Hunter Harris: Mm-hmm.
Kevin Callahan: it became like a focal point for people to really kind of talk to and talk about.
Hunter Harris: Yeah, actually you reminded me a little bit of one I don't know if I would call this a war story, but back when I was at Sales Loft. god, I I'm trying to get a few people to talk about this on the podcast at some point, but I haven't managed it yet. But so Sales Loft was it locked into this really tight competition with outreach. And so Outreach was having a particular conference, I think it was Unleashed, because the name of the conference Unleashed was super important. Outreach had a giant like I and I think this is like a thing at the time, right? They have these giant boards that would be like, okay, if you tweet hashtag unleashed, it'll show up on the board, right? So what SalesLoft
Kevin Callahan: Yeah, yeah. Yeah.
Hunter Harris: did is they snipe the thing by
Kevin Callahan: Mm.
Hunter Harris: going and doing a puppy adoption event sponsored by SalesLoft and having all of the people going to the puppy adoption event tweet hashtag unleashed right in the middle of the competitors conference.
Kevin Callahan: that's so incredible. That's incredible.
Hunter Harris: Right? And so th right in the middle of the conference, they have this giant board that's just running ads for their biggest competitor, right? And they end up having
Kevin Callahan: Wow.
Hunter Harris: to shut down the whole board. I mean, don't quote me on this, but I my recollection is that they had to shut down the whole board and just be like, Cool, we can we can't do this in the middle of the conference, right? And like
Kevin Callahan: Yeah. That's so awesome.
Hunter Harris: I personally I've never really liked I feel like social media in general. I don't feel like I've really like gotten it, but that's just one of those memories that is just fully cherished of like, my god, I would never have thought to do something like that.
Kevin Callahan: Yeah.
Hunter Harris: And platforms like Twitter make all of that possible. But I I guess shifting gears a little bit, right? So you were at Twitter for a number of years, right? But you were not at Twitter now. well I guess it's X now, so obviously. But you made the leap to startups, right? So what was it about Twitter or about Coinbase that started to make you feel like you wanted to take that sort of leap?
Kevin Callahan: Yeah. So growing up I always knew I wanted to be an entrepreneur. And I think you know, and I had some early startups or startups that were early in my career and I had a you know, a bunch of flame outs, a a couple base hits. And I I say that if I were to die without having you know, the semblance of a successful startup, I would really regret it. And so it was always in the back of my head, you know, I need to eventually have like a successful startup. And I'm not
Hunter Harris: Mm-hmm.
Kevin Callahan: saying we're successful yet, but I'm on that path. And so there's actually three things that were really important. One was you know, do I have like a particular area, a think I want to solve? And the second one was, do we have like the team and the people around me? And the third was like financially, mentally, my wife, like are we in a good spot? But anyway,
Hunter Harris: Third one super super important.
Kevin Callahan: Yeah, I think I very much misjudge the third one, to be honest. And we can get into that a little bit. But sure. Yeah, for sure. Yeah.
Hunter Harris: yeah, I w I was about to say, do wanna elaborate a little bit? 'Cause that sounds interesting.
Kevin Callahan: So I think a few things. One, you know, love my wife's amazing. I love my wife. And my my thought process at the time was that, well, okay, you know, you're working in big tech. You're making like honestly, you're making like seven figures, everything's great. And in that time frame, too, it's like everything I invested in was like doubling, tripling. I like if I put money in this startup, I was like,
Hunter Harris: Yeah, that whole time period was insane.
Kevin Callahan: I'm a genius. Like I'm just like money's everywhere.
Hunter Harris: Yeah.
Kevin Callahan: I'm like literally, I'm like the smartest man in the room. And you know, money's not an issue, and like, you know, we can just figure things out and you know, all
Hunter Harris: Fix it in post with the cache, right?
Kevin Callahan: funny, yeah, exactly. And also things like You know, I would watch friends leave Twitter and Coinbase and they would raise five million dollars on twenty-five million for like an idea. And it would everything
Hunter Harris: Mm-hmm.
Kevin Callahan: seem simple. By the way, like,
Hunter Harris: It's a different time.
Kevin Callahan: yeah, I know, yeah. And also, like, put a pin in that. What you know, narrator comes in, it wasn't that simple. But anyway, for them it
Hunter Harris: Exactly.
Kevin Callahan: looked really simple. and so
when I went out and started, my assumption was, okay, like I'm gonna go and raise five million bucks. We're gonna go and do what we want to do. I can pay myself well. Like not like, you know, not million dollars, but like I'm not zero. and we're not a wrong above joke. I'm a little too
Hunter Harris: Right. You're you're not on a ramen budget, right? Like you're you you're living.
Kevin Callahan: yeah, I'm a little too old and now I have a kid. So Ramen is a little bit hard to anyway. The problem
Hunter Harris: Yeah. Right.
Kevin Callahan: was when I went to go raise money, the world had ended, right? Like literally there was that Three or six month window where Facebook started laying everybody off, Google started for the first time ever, same with Google, Silicon Valley Bank
Hunter Harris: This was
Kevin Callahan: that had
Hunter Harris: was this SVB dying so this was what? Early twenty twenty three?
Kevin Callahan: Yeah, essentially. Yes. Yes. So
Hunter Harris: 'Cause I I was I had a whole adventure with the S V V stuff too. That was
Kevin Callahan: Yeah, yeah.
Hunter Harris: that was a spicy couple days.
Kevin Callahan: Yeah. And so and there was a lot of knock on effects that people probably forgot. But the reality is,
Hunter Harris: Mm-hmm.
Kevin Callahan: when you go and raise money and the VC is just like, my money's like, you know, locked up. Wait a minute, like some of our startups are gonna lose their money. and you know, there's layoffs so people are not like it basically on all and by the way, like the Facebook stocks of the world, the Fang stocks, like the MAG seven stocks, they got cut in half. They were down by like fifty at or fifty percent.
Hunter Harris: Mm-hmm.
Kevin Callahan: Over the last you know, over
Hunter Harris: That's brutal.
Kevin Callahan: l yeah. So raising money was hard. It was like and I'm like out here like
Hunter Harris: And and I mean, raising money is generally hard on a good day, right? Like
Kevin Callahan: Yes, yeah. Except for that like one year window where apparently it was very easy. But anyway. So so basically, yeah, like th we started off in not a great start where it was like, this is a lot harder. And we ended up I ended up I ended up being able to raise two and a two two point three million. but there was like that was like brutal. That took like six to nine months and we wanted to, you know, we wanted to raise five and then ended up bringing down to one and some you know, I basically didn't pay myself for like a year and then paid myself like ramen for like another year and then paid myself ramen and a little bit extra and now finally we're getting to a point where like but the problem is over the course of like you know like two and a half years your wife is the one that's like my income that really matters right like
Hunter Harris: Mm-hmm.
Kevin Callahan: and as you know again we have a loving relationship and I would say that like the male female dynamic is a thing, right? You know you know my
wife is like I didn't sign up for this.
Hunter Harris: It it is a thing. Yeah,
Kevin Callahan: Right, I didn't sign up to be the breadwinner. The fuck is this?
Hunter Harris: exactly. That's exactly it. Like it's like maybe I am actually good to do this, but ac I did not sign up to this. Like
Kevin Callahan: Yeah.
Hunter Harris: all of a sudden I'm the br like, wait, what? Reah.
Kevin Callahan: You didn't ask for this. Yeah. She's like, I did not ask for this. This is not what you told me. and
Hunter Harris: And like even if she's well set up for that, like being the breadwinner, it's just like even if you're set up well for it, it is a stressful proposition, especially when it's when
Kevin Callahan: Very stressful.
Hunter Harris: it happens suddenly and unexpectedly, right?
Kevin Callahan: Yes. And I think things happened so a few a lot of things happened. One was, we so again, remember I'm the ri I'm this I'm rich and I'm so smart. I bought a bunch of pre build condos and they all came new and they're like, you need like, you know, hundreds of thousands of dollars. And wait, I don't have an income, so getting a mortgage is really hard when we have no wake up. So that
Hunter Harris: Yeah, ups.
Kevin Callahan: happened. Oops, and even like again, my my wife's happily employed also in Keck. And she makes good money. But you know, like there's days where she's like, I hate my life, I don't want to work here, I wanna change. And it's like, Yeah, I don't know if like you can right now.
Hunter Harris: Can can we do that a little bit later, please? Cause
Kevin Callahan: Yeah. Yeah.
Hunter Harris: I mean I'm somewhat in a similar boat because I'm
Kevin Callahan: Yeah.
Hunter Harris: I'm on my entrepreneurial journey, my wife is on her entrepreneurial journey, and it's a whole it's a whole thing. It's I mean I love
Kevin Callahan: Thing. It's a thing.
Hunter Harris: it. I signed up for it, but it's it is in fact a whole thing.
Kevin Callahan: Yeah. I think there were a few times where and again, if you remember the earlier part of my story, I'm like, I always wanted to be an entrepreneur. This is like part of my thing. And I remember a few times I'm sitting in like, you know, San Francisco, it's like crisp air, and I'm like, I'm being such a such a baby, like just like, you know, go hit the gym, go hit the phones. Like you're you're you're so blessed to be here. Yeah, you're blessed to be here. Coffee's for closers.
Hunter Harris: Yeah, just close, baby. Coffee is for closers. Shut up and shit pretty much to yourself, right?
Kevin Callahan: Yep. ABC. So I think like you just have to remind yourself, like, I signed up for this. The thing is, like I said, my wife did not sign up for this. We're now finally
Hunter Harris: Right.
Kevin Callahan: within the last like ninety days at a position where like, okay,
Hunter Harris: that reset?
Kevin Callahan: kind of, yeah, because like, you know, the first year nothing. Second year, and you're dealing with like again, we're very, very blessed to have like savings and have money, but like you're kind of like my friend, there was a point maybe tw The day the years are all getting all blurry. But let's say 2024. For like a year, I was maxing out the credit cards, 50K, paying it down,
Hunter Harris: Yeah.
Kevin Callahan: maxing out the credit cards, paying it down, right? And again, like I didn't even tell my wife all this stuff. I'm like, you know what, babe, everything is fine. Meanwhile, I'm like literally maxing out the credit. Yeah,
Hunter Harris: Things gold it, no questions.
Kevin Callahan: everything's great. And again, you know, I'm fortunate that we have like a 401k that we can dip into, which we did a couple times. But man, this is not what she signed up for, right? Like, and I
Hunter Harris: Yeah.
Kevin Callahan: don't think a lot of founders are honest about how hard things are. I think you see this like we raised seventy five million dollars, everything's amazing, everybody's high fiving, Sequoia led, we're we're geniuses. Not a lot of people from my experience are like, actually, man, like I was like ripping my hair out and like I actually blew one of my teeth because I didn't know how we were gonna make payroll. So yeah, it's an interesting ride.
Hunter Harris: Yeah, and I mean the the flip side too is you hear about the stories where someone raises like 75 million, but you don't hear any of the stories about all the people that raised zero, right? Or the people that are like, well, I'm good
Kevin Callahan: Yes, yes, yes, yes, yes.
Hunter Harris: I've been grinding for two years, couldn't fundraise, and now I'm going back to a desk job.
Kevin Callahan: Yeah. Yeah.
Hunter Harris: and so like the survivorship bias is tremendous, right? And e I mean,
Kevin Callahan: Also very true.
Hunter Harris: to your point too, like even if you're closing the 75 million, a lot of the time it's like, okay, cool, you closed 75 million on what terms? Like, who
Kevin Callahan: Yeah. Mm-hmm.
Hunter Harris: who are you actually getting slotted into your board?
Kevin Callahan: Yeah.
Hunter Harris: what control are you retaining? Because I guarantee you there's a whole cohort of the 75 million people that are like, Cool, I am no longer the captain of this ship,
Kevin Callahan: Yep. Yep. I think there aren't enough again, like avenues. So I don't know, podcasts or where people are telling the truth about how things work. Cause even even what
Hunter Harris: Yeah.
Kevin Callahan: you just said, you raise the money. you don't talk about, yeah, like what is the prep stack, like what are the term rooms, like who's like what's what's happened, what are the horror stories? And actually, you know, one on one, I talked to people, I had a really really I had a sandwich yesterday with a founder. He exited at about a hundred million dollars like from the high like that's like the you know the big like tech crunch number.
Hunter Harris: Mm-hmm.
Kevin Callahan: But like actually
of that, I don't think I think he has zero right now, right? There's like all these and we can
Hunter Harris: Mm-hmm.
Kevin Callahan: get in like it's not really my story to tell, but there's all these reasons why, you know, he was at it for 10 years, right? And it's like, you know, that's sort of it, right?
Hunter Harris: Exactly. I mean so many people are like, yeah, I'm gonna get in, I'm gonna phone raise, I'm gonna get out, it's gonna be two like two years, two and a half years max, and I'm gonna get f like a hundred million dollars and I'm like, good luck.
Kevin Callahan: Hmm, mm, that's hard. Yeah. I talked to more founders, to be honest with you, that are like, I'm trying to fundraise that's like impossible. I will say that my experience,
Hunter Harris: Yeah, especially right now.
Kevin Callahan: yeah. My experience with fundraising and just people like helping people try to think through it, it's not complicated, but it's very hard. So for our fundraise, I've been public about
Hunter Harris: I think that's a good way to put it.
Kevin Callahan: this. Yeah. This pre seed and the seed. We've raised seven and a half million total.
Hunter Harris: Mm-hmm.
Kevin Callahan: I spoke to somewhere between a hundred and fifty and two hundred VCs each time. probably on average three to four calls. So call it like you know, like six hundred, seven hundred calls. because some people have to have multiple. One person
Hunter Harris: Course.
Kevin Callahan: has one, one person has ten, you know. and assume it's like 30 minutes on the calls and then assume all kind of like the back and forth and you know, all the you know the due
Hunter Harris: The scheduling.
Kevin Callahan: diligence everything. It's e it was easily like a thousand hours of of work
Hunter Harris: Mm-hmm.
Kevin Callahan: to do our f our fundraise and you know, and
Hunter Harris: I believe it.
Kevin Callahan: then you're running a company and everything like that. So yeah, that's probably and also like I said, you know, you have p like every almost every VC is gonna make it seem like they're interested and then, you know, they ghost you or they don't wire after they've
Hunter Harris: Mm-hmm.
Kevin Callahan: signed. I've had I can tell I have every story. It's crazy. But I think
Hunter Harris: Absolutely.
Kevin Callahan: you're the first time founder, you're like, all I see is the 75 million dollars. It seems super simple. I'm a loser. And the answer is no, you're not a loser. things that I would say is like, hey, there's unlimited pre seed VCs. There are tens of thousands of them. You will run out of days before you run out of like VCs. So as long as you are fire and committed and have your process, you will raise money. It's just a matter of how hard you're willing to work for it.
Hunter Harris: That's a good way to put it, and I like that attitude too.
Kevin Callahan: the one thing I'll say is again,
Hunter Harris: Sure.
Kevin Callahan: it's not complicated. There are lots of way like resources online where they say, Hey, here's
Hunter Harris: Mm-hmm.
Kevin Callahan: kind of how you do it, here's the process. The one but when I do talk to some founders, and it's happened a few times over the last like, you know, couple months, where I explain, I'm like, Hey, it took me a thousand hours, it took me like two hundred calls or sorry, two hundred V C's, hundreds of calls. and the founder's like, I'm not doing that. Like, while you're pretty much fuck. Like there's no like you're
Hunter Harris: Yeah, good luck.
Kevin Callahan: and by the way, if that's not what you're willing to do, there's no way you're gonna like crush it when you're you know, things are hard.
Hunter Harris: Yeah, exactly. I I was gonna ask actually the the question that I was trying to remember. so I'm talking to a lot of founders that are trying to raise just with straight up cold outreach to BCs. What
Kevin Callahan: Mm-hmm.
Hunter Harris: I mean, ballpark gut check percentage was like hot lead warm intro, cold outreach for the fundraising that you were doing?
Kevin Callahan: So cold outreach did work. we had
Hunter Harris: Of course.
Kevin Callahan: we got a we got a couple of checks via the cold outreach, and the cold outreach that like converted those people ended up making other, you know, connections. usually what you need and and honestly it's funny, like I'm very blessed. I'm an LP on some funds and none of those funds put any money into us. So it
Hunter Harris: Ha ha ha.
Kevin Callahan: So I don't know, like I mean, for somebody that should have some like you know, extra connections, it
Hunter Harris: Yeah.
Kevin Callahan: was only so helpful. you you know, clearly you want to get warm all the way down to cold, but you can still convert with cold, and then also there's just ways to get on people's like radar. and you know, in terms of trying to get the ball rolling, you know, hopefully you know other founders, preferably some of them have raised, you can Try to ask them to start making intros and get the ball rolling really hard. But you know, you're basically doing everything as well. so, but one thing people think is like, cold outreach doesn't work, and the answer is that is untrue. The only caveat I would say is
Hunter Harris: Absolutely.
Kevin Callahan: you don't want to just like send an automated email to a thousand VCs. Like you want to like target and go properly. so that's probably it's more so does cold outreach work? Yes. Does mass cold outreach work? It's harder to say.
Hunter Harris: Yeah, I was gonna say 'cause I had a founder ask me about like And this is a bit more sales focused, but I mean pitching VCs is just a different type of sales. Like, for your cold outreach, are you doing automated AI-generated messages? And I was like, Lord have mercy, no, my ACD is millions of dollars. Like, if I can't
Kevin Callahan: Yeah. Yeah.
Hunter Harris: be asked to spend 15 minutes researching someone and like
Kevin Callahan: Yeah.
Hunter Harris:
crafting some form of targeted outreach, then what am I doing, right?
Kevin Callahan: Yeah, I agree with that fully. I think that I I'm I'm I'm hopeful that this time of AI slop is is short lived because the AI slop got really bad. Like I feel like even like my teammates were sending me like forty seven page documents that's all A I'm like, dude,
Hunter Harris: lord.
Kevin Callahan: if you're not gonna read this, I'm not reading this. Like I'm not your like flesh router. Yeah. So so I think that's anyway, keep going, sorry.
Hunter Harris: Exactly. I mean I was just gonna say I don't know. I don't want to put it this way, but I love your optimism. There's the slot thing is so interesting. Humans are fascinating and weird because I think, you know, obviously most people dislike slop. There's a real demographic of people out there that like slop and
Kevin Callahan: I yeah, like videos and I I I I I agree with that. I just think that like it got really bad to the point where, you know, people were sending me like ten pages of obvious slop and I'm like, Well this is not gonna convert. And also like, you know, those of us that are receiving said slop I think are starting to a like really, you know, viscerally push against it. but also I think, you know, the spam filters and everything are starting to really catch on. But
Hunter Harris: The spam filters have gotta put pin in this at some point. But i I mean, to your your point about this, there
Kevin Callahan: They gotta catch up, man. This is ridiculous.
Hunter Harris: there are pe I am very much not in this demographic, to be clear, by the way, but there's people that I've met, 'cause I talk to a lot of people, who are like, yeah, just don't talk to me, just basically slop at me and I'll throw it into my LLM and decode it, etcetera. And I'm like
Kevin Callahan: I do sort of see that, but I'm like, what am I supposed to do? Like I don't do that, so I'm like you're just sending me s like literally like I'm not sure what's supposed to do with this.
Hunter Harris: Exactly. And honestly for the s to your point about slop too, like if you're gonna send me a whole bunch of slop, just send me the prompt. Just start with the the targeted thing. Just send me the original thing and don't expand it out to something gigantic. And I can take it from there. Like I can do all the
Kevin Callahan: Yeah.
Hunter Harris: whole process with my own LLM, right? So it's it is wild. It's so wild.
Kevin Callahan: Yeah, I don't know. I feel like Yeah. But yeah, getting back to the outreach thing, I think usually it's you see somebody has invested in a deal that feels, you know, in your space, or you see like somebody commenting about something that makes sense on LinkedIn, for example, and then you send them like, Hey, this is what we're up to. It sounds like something might be in your in your wheelhouse. Also you have to make sure your LinkedIn looks good too, where you look
Hunter Harris: Course.
Kevin Callahan: like somebody you'd want to invest in, which again people don't always think of. and then yeah, we've seen that convert a few times. Which and also, by the way, once you start every VC also has their systems in place to find the next startup, right?
Hunter Harris: Mm-hmm.
Kevin Callahan: So they're looking for signals. and you know the signals vary, but it could be, again, somebody leaving open AI and write stealth
Hunter Harris: Mm-hmm.
Kevin Callahan: on LinkedIn or like building something new and like that person is gonna get like hit like through their their automations. But I think
Hunter Harris: Mm.
Kevin Callahan: that you know once you get the ball rolling, we've had hundreds of thousands of dollars invested in us via outreach, like people reaching out to us because
Hunter Harris: Mm-hmm.
Kevin Callahan: the ball is going.
Hunter Harris: Well Kevin, I wanna be respectful of your time. Do you wanna plug your pluggables?
Kevin Callahan: So yeah, so we're we're hopscotch, we're building an AI router. The concept is that we are able to hold on to your contacts, we're able to like save you money. we've been building it for the last couple of years. we are experts in routing. We've we've done it with lots of different you know, high performance data. But hopscotch labs dot ai and Yeah, I would love to be able to win your business where we're a group group of people just like kicking butt on the AI side.
Hunter Harris: Yeah, I mean I'm working on my own software factory, so we might be having some product based conversations in the future.
Kevin Callahan: for sure. Come on in and use it. You can you should definitely use hopscotch, it's a great product.
Hunter Harris: Yeah, I mean some of what it looks like it's doing is immediately relevant to some of the problems that I have. So
Kevin Callahan: Yeah.
Hunter Harris: we're we're gonna see what we can do. well Kevin, thank you very much for joining us everybody. I hope you've enjoyed this conversation. I've obviously enjoyed the hell out of this conversation. great way to spend a Friday. hope y'all learn, hope y'all grow, and I hope you all have a fantastic day. Peace.