This Meeting Could've Been a Podcast

Season three Jess is not season one Jess. Same goes for Josh. Raising $10 million will do that to a person. 

Josh hits the road to raise Vector's Series A. Weeks later, he's back full of ideas. None of them related to Vector's actual business.

While Josh is away, Jess and the leadership team stop waiting for permission. They figure out what to do without him. Turns out: they know what they're doing.

Back on the investment front, Josh sends a telegram. Complete ye olde English prose from a plane at 3 am.

Hear how Josh used the whispering game, a New York meeting slot he hadn’t booked yet, and high school lunch table vibes to get through the roadshow.

Get to the good stuff:
[00:00] Josh returns from the investment roadshow with three groundbreaking business ideas, all of them “great.” Sigh.
[02:24] The raise isn't the win your LinkedIn feed thinks it is — why Josh resisted until he couldn't.
[04:02] Jess explains how they gathered customer feedback for the raise three months after a hard pivot. Alex said I've got this... and delivered.
[07:30] Jess coined the phrase Deep Ass Financial Dive (trademark pending), and yes, it is exactly what it sounds like.
[09:57] Churn versus Optics: Josh admits letting optics win for the fundraising window.
[11:57] Josh explains how having the biggest quarter in company history changes the room.
[13:10] Fundraising sucks. Josh does not recommend… kind of.
[15:22] Josh’s investor playbook: practice reps, whisper campaigns and an imaginary New York slot.
[20:46] Dad is out of the house. Jess learns to stop asking for permission.
[24:01] Jess starts feeling like Josh is at war. Josh sends her a telegram from the fundraising front... in ye olde English.
[26:00] Josh turns Fridays into grenade drops. We need to become an agency. AI is replacing us all. Something else about AI. Goodbye.
[28:30] Affirmations break. Live, laugh, lower CAC.
[29:05] The $10 million question… why SignalFire and HubSpot Ventures said yes.
[33:33] Jess and Josh ditch the press release for their Series A announcement. They were over the theater, so naturally…cue the 90’s sitcom-style video.
[37:59] Jess pitches real ghosts (naturally).

This Meeting Could’ve Been a Podcast is a Vector production.
Filmed and produced by Sweet Fish.
Editing by Handy Man Edit.
Show notes by Content10x.
Music by Peter McIsaac Music.

Creators and Guests

JC
Host
Jess Cook
Head of Marketing at Vector
JP
Host
Joshua Perk
Co-founder and CEO at Vector

What is This Meeting Could've Been a Podcast?

This Meeting Could've Been a Podcast drops you smack dab in the middle of the closed-door sessions where Jess Cook (Head of Marketing) and Joshua Perk (CEO) are working to turn their company, Vector, into B2B marketing’s next big thing.

In each episode, they tackle a real, strategic decision together—"Should we hire an agency?", "Should we push free trials or demos?", "What are we going to do with all the swag Josh bought?!"—dishing out pros, cons, knowns, unknowns, wins, challenges, and stories along the way.

Come for the big picture strategy and day-to-day tactics, stay for the jokes that make HR nervous.

[01:00:00] Jess: Welcome back, Josh. How was the series A roadshow? I feel like you were gone forever.

[01:00:04] Josh: It was great, and we raised the money, but I think we should become an agency.

[01:00:08] Jess: Oh, okay. Really? Like, I guess I could see us adding a services layer.

[01:00:12] Josh: Wait, wait, wait. What if you could talk to your ads?

[01:00:15] Jess: Ooh, like an MCP or a chatbot?

[01:00:17] Josh: Actually, we should just make shoes

[01:00:26] Jess: Hey, Josh, remember that time when you went and raised a series A and came back [01:00:30] an absolute monster?

[01:00:32] Josh: The Bay Area will change you, baby. Just b- chew you up and spit you out. Totally different person.

[01:00:38] Jess: Oh my gosh. You came back with a lot of ideas.

[01:00:41] Josh: A lot of ideas. We- A lot of opinions ... a l- a lot of bad ideas.

[01:00:44] Josh: Yeah. It, it was, it... We'll go through the whole sort of raise story, but I think, like, this, right? Yes. Episode one of season three is gonna be all about, like, we grew up over the last, you know, year or- Yeah ... or six months, and, uh, raising money [01:01:00] was part of that. But sort of all of the changes that came in the company, getting a board member-

[01:01:05] Jess: Yeah

[01:01:05] Josh: having lots of employees. Like, we really... Season three Jess is not season one or two Jess anymore.

[01:01:10] Jess: No. And same with you. Like, season one and two Josh, like, season three Josh is, like, a different man. But, like, in a good way, right? Like, we're growing up.

[01:01:18] Josh: Kind

[01:01:18] Jess: of. This is our coming of age story. Would

[01:01:20] Josh: you say I'm more of an asshole now than I was

[01:01:22] Jess: two seasons- You're the same kind of asshole.

[01:01:25] Jess: But a lovable one.

[01:01:26] Josh: That's valid. That's valid.

[01:01:29] Jess: Yeah. Yeah. I think this whole [01:01:30] season, like, every episode we're gonna talk about something that we now have the ability to do-

[01:01:34] Josh: Yeah ...

[01:01:35] Jess: that, um, you know, we feel very confident in moving forward because we did the Series A, which is really exciting.

[01:01:41] Josh: Yeah, and I think our stories are gonna get more relatable this season.

[01:01:44] Josh: I know the first two seasons, people would stop us and be like, "Jess, you're so lucky. Your CEO just gets marketing." And you're just, like, going on vibes. And I think now- ... now we actually have, like, people in the room that expect- Yes ... what our audience and our customers w- expect as [01:02:00] well, which is pipeline and results.

[01:02:01] Josh: And so now you're starting to get a new version of me, which has this, like, pressure around marketing. Yeah. But I think we're still balancing it pretty well.

[01:02:08] Jess: I think so, too, and a new version of me that, like, has to get good at math- ... and, like, kinda has to figure out if things are working or not. Y'all,

[01:02:14] Josh: she's not good at it.

[01:02:15] Jess: It's- I know. It's, uh, rough. I'm really good at English and words. I've,

[01:02:20] Josh: I've seen her search history. It's like, "What is pipeline?"

[01:02:24] Jess: There's, like, that percentage change calculator. Like, I u- I Google for that thing.

[01:02:29] Josh: Oh, I love it.

[01:02:29] Jess: I should [01:02:30] just bookmark it at this

[01:02:30] Josh: point. Yeah, me too. I know the exact one you're talking about.

[01:02:32] Josh: It's this little, like, tiny calculator on the left side. It's

[01:02:34] Jess: hideous. Yeah. There's no design to it. Does everything you need it to do, nothing more. That thing's

[01:02:38] Josh: probably got the most site traffic in the world.

[01:02:39] Jess: It's got to. They

[01:02:40] Josh: should throw ads on that thing.

[01:02:41] Jess: Yeah. Maybe they do. They probably do. Probably do.

[01:02:43] Jess: If they were smart.

[01:02:45] Josh: So we raised money.

[01:02:46] Jess: Yes. We raised money. Let's talk about it. Let's go back to the beginning of, like, what happened when you realized, "Okay, we actually probably need to raise"?

[01:02:54] Josh: Yeah. There was a couple things. So I think the first thing that was important for us is, like, we're, we're not a [01:03:00] Bay, a classic Bay Area company.

[01:03:01] Josh: Yeah. Like, we, we didn't wanna raise just for, like, the headline. We didn't, we actually didn't think it was a positive thing, right? Yeah. I think there's this, like, misinterpretation because there's all these, like, LinkedIn posts of, like, "We raised millions of dollars at billions of dollars evaluation." And that, that feels like the winning moment, and for us, it's not it, right?

[01:03:17] Josh: Like, like, the money is fuel to keep building the thing that ultimately matters. But so for us, like, we, we didn't end 2025, like, really wanting to raise, but there was a couple things that we saw. We were like, "Okay, this could be a good [01:03:30] idea." Yeah. One was our team was growing a ton.

[01:03:32] Jess: Yep.

[01:03:33] Josh: I think you have, like, five people on your team?

[01:03:35] Josh: We have

[01:03:35] Jess: a five-person marketing team now.

[01:03:37] Josh: That's wild. Yeah. So, like, the team was growing. Like, you're just one of oth- many departments also were, were growing as well. So, like, we just knew that more money equaled more security- Yeah ... for employees, which is important. Um, we really started to, like, kind of find our sea legs towards the end of the year in, like- Yeah

[01:03:52] Josh: product direction. And, you know, we still had a lot to work on, but we could kinda start to see, like, man, there's, there's a market here. There's an opportunity to build [01:04:00] something really big. And, like, that costs money. Yeah. Um, and so yeah, the, the writing was just on the wall. And then finally, like, most startups aren't profitable.

[01:04:07] Josh: And so, you know, you look at how much money you have in the bank, and you're like, "Well, it's probably time to, to raise." So-

[01:04:12] Jess: Yeah ...

[01:04:12] Josh: we knew it was time.

[01:04:13] Jess: It was time. Yeah. Yeah. To raise a Series A-

[01:04:16] Josh: Yeah ...

[01:04:16] Jess: you can't just go out and be like, "Hey, we need to raise a Series A." Like, you have to get the business to a point Where you feel very confident going out to raise that series A.

[01:04:25] Josh: Yeah.

[01:04:26] Jess: So let's talk a little bit about the things we had to do to be in the [01:04:30] position to go out and do that.

[01:04:32] Josh: So it's, it's funny. Raising, raising money is It's an awakening experience. You learn a ton about the world, and you, you realize really quickly, like, venture capital just operates at a very different frequency than the operators in a business.

[01:04:47] Jess: Oh, yeah.

[01:04:47] Josh: Right? For them, they're like, "We don't really care what you're building. We just wanna know if, like, you're a better vehicle to return the money plus 100X more than what we gave you." Yes. And when you start to think about it that way, you [01:05:00] realize you're not competing against other marketing tools or other security tools, you're competing against every other company that's trying to raise money- Yeah

[01:05:07] Josh: from the Valley. And so because of that, there's, like, all these things that you just have to make sure look real good to basically convince these investors that, like, you're the best vehicle for them to invest in. Yep. So it was like churn, and optics, and customer stories, and pipeline, and I don't know if you want me to be listing them all like this-

[01:05:26] Josh: or if we were supposed to tell, like, the stories one by one. [01:05:30]

[01:05:30] Jess: That was a great intro, Josh. Let's break those down.

[01:05:33] Josh: Awesome. Yeah, like, okay, so, so yeah, there were all of these things that, like, we needed to, like, make look really good on paper. Yeah. What was, like, the first one that I came to you saying, like, "Okay, this is what we need to do s- for me to raise?"

[01:05:46] Jess: For, for marketing, it was like we need great customer stories. Yeah. We had gotten a couple under our belt. Mm-hmm. Right? Uh, but it, you know, I mean, you go back to season two, we had just gone through a pivot.

[01:05:56] Josh: Yeah.

[01:05:57] Jess: And we had basically, [01:06:00] you know, three months had gone by at that point, right? Yeah. So it's like to find customer stories that were like they're seeing great things happening after three months- Yeah

[01:06:09] Jess: uh, was like, ooh, that's a good challenge. Okay, let's go out and find the folks who are doing the most with the product after just three months of really having the new version of Vector kind of, uh, at their disposal.

[01:06:20] Josh: And that was, like, a totally different, um, I don't know, swim lane for us in marketing.

[01:06:25] Josh: Yeah. Right? We, we'd spent, I mean, up to that point, all of our energy was in, like, net new [01:06:30] customers- Yep ... pipeline generation. All of a sudden we sort of had to, like, dust off this, like, product marketing and customer marketing- Yes ... gene that we didn't have before.

[01:06:37] Jess: Yeah. And Alex Verdin, bless her- ... was like, "I've got this."

[01:06:42] Jess: Yeah ... and went out and started, like, interviewing customers and understanding, like, the wins they were having and the returns they were seeing. Um, she built a, a ton of playbooks, a bunch of case studies, and so that was really helpful, one, like, just to arm our sales team- Yeah ... uh, with all of that information.

[01:06:58] Jess: I think that would've, that would've been content we [01:07:00] would've needed anyway. Yeah. We probably just did it, like, a touch faster. Mm-hmm. Um, because we needed to feel very strong and ready for the series A, but it was also really hel- helpful content for the sales team to be like, "No, look at what this customer has done.

[01:07:12] Jess: Look at what this customer has done." So, um, I think we, we went out and really figured out, like, what are the people who are using our product in the way that we hope they will- Yeah ... which is, like, building ad audiences, and revealing who's on their site, and being able to, like, action on that information.

[01:07:28] Jess: Yep. And, you know, what kind of returns [01:07:30] were they seeing? So that was, I think, the first thing you tasked us with.

[01:07:33] Josh: Yeah. I had to have all these, like, pocket stories, right? 'Cause the first thing they would ask is sort of li- Like, tell me your biggest customer and how they're using it and, and sort of what value- Yep

[01:07:42] Josh: they're getting. And so marketing really supplied me with all of that. But then there was this other side which was like, "Okay, cool. Put all the soft fuzzies away. Like, give me your numbers."

[01:07:50] Jess: Yep.

[01:07:51] Josh: And I felt like that was, like, kinda new for us.

[01:07:53] Jess: Totally.

[01:07:54] Josh: At least in marketing. Oh,

[01:07:55] Jess: yeah.

[01:07:55] Josh: Because one of the things that, like, works for us is, like, we do stuff like this- Yep

[01:07:58] Josh: which is, like, kind of, like, [01:08:00] hard to measure, uh, build our community. And all of a sudden it was like, "Well, prove it."

[01:08:05] Jess: Yeah, yeah. Yeah. Man up. What's going on? Man,

[01:08:08] Josh: man up.

[01:08:08] Jess: Yeah.

[01:08:09] Josh: Where's the pipeline, baby?

[01:08:10] Jess: Right, yeah. So yeah, it was very much like we had to do, uh, what I like to call, scientific term, deep ass financial

[01:08:17] Josh: dive.

[01:08:18] Josh: Deep ass financial TM. TM.

[01:08:20] Jess: Trademark.

[01:08:21] Josh: Deep ass financial dive. You'll

[01:08:22] Jess: find that in the textbooks someday, guys.

[01:08:24] Josh: Just a picture of Jess, Professor Jess, deep ass financial dive.

[01:08:29] Jess: Um, [01:08:30] because we'd never... I mean- You and Nick had done that. Yeah. You understood the health of the business. Yeah. But in terms of, like, real, like, marketing dollars in and ROI out, we operated on vibes for a lot of 2025, which worked for us.

[01:08:44] Jess: Yeah. Um, we were 100% inbound. We didn't do any outbound. We did very little paid. I think for the entire year of 2025, we spent maybe 40 grand on paid. Wow.

[01:08:54] Josh: Yeah.

[01:08:55] Jess: Um, and so all of that was just organic and just really good content, [01:09:00] SEO, GEO, like, all of those- And it worked ... types of... And it worked. Yeah. And then we get to the end of the year, and it's like, "This isn't probably gonna scale."

[01:09:07] Josh: Yeah.

[01:09:08] Jess: One, we're, like, at our, kind of, bandwidth for creating organic content like this. Yeah. Um, besides being able to, like, you know, use Claude and kind of scale that side of things, but, like, actual human written, you know, case studies and really good, like, video content like this, like, we're, we're at the...

[01:09:24] Jess: We're, like, really at the margin here.

[01:09:26] Josh: Yeah.

[01:09:27] Jess: Yeah. Um, and so we never [01:09:30] really needed to do, uh, kind of a one-to-one comparison of, like, what's going into it and what's coming out because we weren't doing anything super trackable to begin with. Yeah. And so, but, but investors don't really care about that.

[01:09:43] Jess: Mm-hmm. They need to know- Mm-hmm ... like, what you're putting in and what's coming out of it. Yeah. So we had to s- we had to go in and kinda figure that out.

[01:09:49] Josh: We had actually kind of drawn a line in the sand that we didn't wanna do what we were calling, like, performative marketing. Yeah. Like, we didn't wanna do things for the purposes [01:10:00] of, like, making it look like everything we were doing was tying to pipeline.

[01:10:04] Josh: Right. And we kind of accepted that, like, not everything was gonna be measurable. And in fact, later in the, the season, we'll, we'll talk about your demand gen marketer and- Yeah ... your search for one. Um, but spoiler alert, we eventually found one, and this person's, like, first question to me was sort of like, "Hey, when I bought Dreamdata, one of the things you said was, like, 'Don't buy it for the purposes of performative marketing.'

[01:10:25] Josh: Like, what did you mean?" And I, I simply, like, didn't want us to [01:10:30] have to do what we literally did for series A, which is, like, tie everything we were doing- Yeah ... back to, to dollars because we all know marketing doesn't work that way. But for, like, this brief period of time, we had to, like, tie everything back to dollars.

[01:10:40] Jess: Yeah. We had to figure it out, um, which was, you know, harder than... As hard as it sounds, I think, because it's like these types of things that we're doing, they're not something that's like, "Oh, someone listened to the podcast," and then immediately-

[01:10:53] Josh: Yeah ...

[01:10:53] Jess: clicked on book a demo. Like, it doesn't work like that.

[01:10:55] Josh: By the way, some, some investors didn't understand that.

[01:10:59] Jess: Yeah.

[01:10:59] Josh: Like, [01:11:00] I, w- in my, my slide deck, like, one of the first five slides was team. And I was, like, very clear with investors, like, "Hey, we're doing something really special on the marketing side. Not everything we're doing is measurable." Um, you know, we had your picture, and Sarah's picture, and Alex's picture basically saying, like, "Hey, this is our strategy."

[01:11:18] Jess: Yeah.

[01:11:18] Josh: And some people didn't get it. And, like, those were the rooms I walked out of, and I said, like, "If you don't get that, then, like, you're definitely not the right partner

[01:11:24] Jess: for us." Yes, absolutely. I love that. Thank you. You're welcome. Thank God.

[01:11:27] Josh: But I do need pipeline deals.

[01:11:29] Jess: I know. [01:11:30] Wait. Where is it, guys?

[01:11:31] Jess: Help me. All right, what else did we do to get ready? Churn was a big one.

[01:11:35] Josh: Yeah.

[01:11:36] Jess: So we had just come off of a pivot.

[01:11:37] Josh: Mm-hmm.

[01:11:38] Jess: Um, and we had some customers who had joined us for the original kind of version of Vector-

[01:11:44] Josh: Yeah ...

[01:11:44] Jess: that were using us for reasons that after the pivot didn't quite make sense. Mm-hmm. And so there were, you know, understandably, a number of customers who were like, "This, this use case really isn't what we want."

[01:11:56] Jess: Yep. Um, "This isn't kinda what we signed up for," understandably, again. [01:12:00] Um, and so yeah, we had to kinda figure that out a little bit. Yeah. Can you talk me through some of the things that you had to do with, like, customer solutions to make that happen?

[01:12:07] Josh: There was, like, two waves of how we focused on retention and churn, and I want to explain why there were two waves.

[01:12:14] Josh: 'Cause I think there was this, like, thing we did in the business where pe- like, some people inside the company were like, "That doesn't make sense," and they were right. Yeah. So, like, wave one was we, we did the right thing, which was we sort of fired or parted ways with customers that we just weren't driving value for.

[01:12:29] Josh: Yeah. We knew we weren't going [01:12:30] that, the, the right direction on the product for them anymore. We did that sort of earlier on before the raise, like six months out. Yep. And then that was the right thing to do. And then sort of, like, a quarter or two before the raise, we, like, stopped letting go of bad customers.

[01:12:45] Josh: And everyone internally was like, "Why?" Right? Like, we've done the right thing. Like, we're letting go of folks that, you know, we're not driving value for. Like, w- why, Josh, are we, like, selling everything at all costs? Why are we retaining customers? Yeah. And we almost had to have this, like, honest [01:13:00] moment with the company where we were like, "You're right," right?

[01:13:01] Josh: The right thing to do as a business is, like, not the sort of charades and optics for fundraising, but the reality is, is, like, we're now in a window that is- Yeah ... sort of this, like, look back period of, of time that when I go raise, they're gonna be looking at the last six months of churn- Yeah ... and retention.

[01:13:18] Josh: So we, like, have to keep these customers. So- Yeah ... so phase one was sort of identifying where the right customers were and sort of parting ways, and then phase two was, like, all hands on deck. Keep, keep retention- Yeah ... as [01:13:30] strong as possible.

[01:13:30] Jess: Absolutely. I think above everything and the thing that, like, the company as a whole was really focused on-

[01:13:37] Josh: Yeah

[01:13:37] Jess: was hitting our revenue goal that we had set at the beginning of the year. Uh, even through a pivot, even through, like, knowing we were gonna be going into this Series A raise, like, we knew we had to hit this revenue goal for that Series A raise to even happen. Yeah. So we, like, really had to step it up at the end of the year and la- like, land these customers, sell, sell, sell.

[01:13:58] Jess: I remember, like, the [01:14:00] December, like, Slack channel for sale, or for, um, revenue was- Yeah ... like popping off. Going off. Like, every day there were a couple ca- contracts getting signed, and it was like, "It's happening. It's happening."

[01:14:11] Josh: We had our biggest quarter in, ever in company history in Q4- Yeah ... right before we went to raise.

[01:14:17] Jess: Yeah.

[01:14:17] Josh: And it's, it was such an example of just, like, I don't know, like- We didn't have everything figured out. No. We are s- we are still to this day wading through product market fit. Yeah. But it was one of those sort of like, okay, you don't have to have [01:14:30] everything figured out to go deliver pipeline, to close deals.

[01:14:33] Josh: Yes. Like, we'll figure it out as we go, and like the team delivered, and it, it set me up for a still difficult pro- like, fundraising sucks.

[01:14:41] Jess: Yeah.

[01:14:41] Josh: But it went as well as it possibly could have gone.

[01:14:44] Jess: Yeah. Okay, let's get into that process, Josh. Yeah. Because I remember, like, you would come back from, you know...

[01:14:52] Jess: You'd come back for like a day real quick. Yeah. You had like a day in between turnarounds of, like- Yeah ... going to New York or San Francisco.

[01:14:58] Josh: Yeah.

[01:14:58] Jess: And I wanna talk about all that, but [01:15:00] I just remember you being like, "This is the most demoralizing process I've ever been through." It's

[01:15:05] Josh: awful. It's like, it's like showing up to like the lunch table and being like, "Am I pretty and can I sit with you?"

[01:15:10] Josh: And they're like, "No." No. They're like, "You're disgusting." It's just, and you just, you know you're gonna sign up for it. Um, it's funny, I remember, I think before the end of the year, I prepped you guys. I'm like, "Hey, this is-" Yeah ... "this is what Q1's gonna look like for me," and it was, i- this was straight from like Y Combinator's advice.

[01:15:26] Josh: They're like, "This could take anywhere from like eight weeks to eight months." I was [01:15:30] like, "Fuck." So, like we just knew it was gonna be like a really laborious process. Yes. Like, you are asking people for millions, tens of millions of dollars. Yeah. And you're trying to convince them that like you are the, the best steward of that- Yeah

[01:15:43] Josh: capital. And so the process is awful. Uh, I

[01:15:48] Jess: Do not recommend. Do- But, you know. Do

[01:15:50] Josh: not recommend. You

[01:15:50] Jess: kinda have to do it

[01:15:51] Josh: sometimes. Yeah, exactly. It's one of those things where, you know you have those moments in your life where you're like, "If I could have like seen how much that would have sucked, I probably wouldn't have done this."

[01:15:59] Josh: Yeah. So I'm glad I, [01:16:00] I'm glad I couldn't-

[01:16:00] Jess: Yes ...

[01:16:01] Josh: have seen it ahead of time. Yeah. Um, but I remember, because like marketing, I was like recording content as we went, right? So like, I like recorded a video on like day one of just like, "All right, it's day one of raising our series A. Like, tonight I'm flying to New York."

[01:16:14] Josh: And then like by like day 97 it was like, "It's day 97 of raising our round." It just got, it just got awful. Yeah. But yeah. I mean, like the, the process essentially, you're, you're traveling to a handful of major cities. Um, for us it was mostly San Francisco, but New [01:16:30] York and Boston also had some, some interesting candidates in it.

[01:16:33] Josh: Um- I was basically an SDR for a month- ... where you're, you're, like, trying to play this, like, popular, like, high school game where it's like, "I'm gonna be on the road, and, like, I'd like to book a meeting with you," but also I'm not asking for a meeting, 'cause if I was asking for a meeting, that sounds pretty desperate.

[01:16:47] Josh: And so you do these things where, like, you whisper to people like, "I'm raising," and then, like, you hope that they whisper to people- Yeah ... and then you get, like, inbounded about it. It's, it's such a game.

[01:16:57] Jess: That was a really fascinating fact that you told me [01:17:00] where it was like you had your kind of first round- Yeah

[01:17:03] Jess: where you went and talked to kind of, like, top-tier-

[01:17:06] Josh: Yeah ...

[01:17:06] Jess: uh, VC candidates. Yep. And, um, through those conversations, those folks kind of spread that news through the, the grapevine.

[01:17:15] Josh: Yes.

[01:17:15] Jess: And then more people come to you because it's like, "Oh, they're smart, and they want to invest? Well, maybe I want to invest."

[01:17:21] Jess: And that was something I don't think I realized was, like, a thing.

[01:17:24] Josh: So there was three ph- there was a phase before that, too.

[01:17:26] Jess: Ooh.

[01:17:26] Josh: We had three phases of how we raised the money. Okay. So, so [01:17:30] first, if we wanna use, like, the high school analogy-

[01:17:33] Jess: Yes, keep going. I love

[01:17:34] Josh: it ... we went out to all the unpopular, uncool people first.

[01:17:37] Josh: Ugh. So we did, like, a, like, a week sprint of the people we didn't wanna raise money from. And we basically just practiced. We, we basically were just like, "We're gonna book. Go, go, go."

[01:17:48] Jess: If you were in that group, now you know.

[01:17:50] Josh: Well, you don't know what week you were a part of. Ooh, right. So you'll-

[01:17:53] Jess: You'll never

[01:17:54] Josh: know

[01:17:54] Josh: you'll never know. But you kinda know. Uh, so yeah, there was this week of people that, [01:18:00] like, we didn't tell them, but essentially it was practice for us. Yeah. It was like, we probably don't wanna raise from, from these people. They, you know- But we

[01:18:05] Jess: gotta get the reps in.

[01:18:06] Josh: Yeah, exactly.

[01:18:06] Jess: Yeah, yeah, yeah. Smart.

[01:18:07] Josh: And, like, and for some of those people, they wouldn't even be offended if we said that.

[01:18:10] Josh: Yeah. Like, we were ... You know, we went and pitched people that, like, mostly, you know, f- r- fundraise, like, consumer services- Sure ... or consumer goods. Like, one of the, the people I spoke to was, like, the person that invested in, like, Quince, Quince? How do you say it?

[01:18:24] Jess: Quince.

[01:18:25] Josh: Quince.

[01:18:26] Jess: Wonderful clothing.

[01:18:26] Josh: Amazing. I,

[01:18:27] Jess: my curtains are from there.

[01:18:28] Josh: They're really nice. My wife has the, [01:18:30] uh, the bedding.

[01:18:30] Jess: Oh, yes. It's super nice. Quince.com, check 'em out. They didn't pay us, but they're lovely.

[01:18:34] Josh: Like, u- use promo code Jess15.

[01:18:38] Jess: I get a kickback. You get a kickback. I don't. I could. Please, Quince.

[01:18:42] Josh: Sponsor me. Um, so we talk to people like that, right? Yeah. And you, you almost, like, walked into these rooms, and, like, I could see on the partner's face, they're like, "I just have to hit my quota of taking meetings."

[01:18:52] Josh: And I was just

[01:18:52] Jess: like- Oh, yeah ...

[01:18:52] Josh: I'm just practicing with you.

[01:18:54] Jess: You're, like, in a weird symbiotic relationship. Yeah.

[01:18:56] Josh: Yeah. We're, like, chewing gum. Yeah. Like, texting while we go through it. Like, we get-

[01:18:59] Jess: [01:19:00] Neither of us wanna be here. Yeah. But, you know, we're hitting our numbers.

[01:19:02] Josh: Five minutes in, I'm just like, "Do you wanna send your, like, EA instead?

[01:19:05] Josh: Like, I'll pitch them. It's fine." Um, so, so that was round one. We, we basically practiced, and that was the... In a second we'll talk about, like, how I came back, like, a complete jackwagon. But, like, that was the beginning of it. Yeah. Because in the practice, you start to get, like, feedback.

[01:19:22] Jess: Yes.

[01:19:22] Josh: Of like, "Well, what if you positioned it like this?"

[01:19:24] Josh: Or like, "AI's really hot right now. Where's your AI story?"

[01:19:28] Jess: Yeah.

[01:19:28] Josh: Or like, "Sequoia just put [01:19:30] out, like, a, a thing about, you know, the next companies will be, like, agencies. Maybe you should be an agency." Which, like, I'll pause there. We'll talk more about that one later. But, like, so you start to, like, get this sort of like, oh, I need to change the story.

[01:19:41] Jess: Yeah.

[01:19:42] Josh: So, like, you, you do a week of that. Then week two, you go to the people that you're actually pretty excited about, but you got intros to. Okay. So you still don't wanna go outbound to anybody. You're using, like, your network. Yeah. Um, and so our existing investors made a bunch of intros to us, and the goal is, of course, that, like, you'll have great conversations with them.

[01:19:59] Josh: Yeah. But that, like, [01:20:00] the people on the street will start talking about- Yeah ... what's going on. And I was really nervous that this wasn't going to work. Our, our partner, uh, Varun, suggested this strategy, and I was like, "I don't know. What if they don't talk? What if we get to week three, and, like, no one's emailing us?"

[01:20:13] Josh: Yeah. "And we're just, like, dead in the water?" Yeah. And he's like, "No, it'll happen." And, like, lo and behold, like, right in the middle of week two, all of a sudden, just like, "Hey," like, "I'm this investor from this firm, and, like, I just wanted to reach out." And it's like, no, you heard. Yeah. You heard that we're raising right now.

[01:20:27] Josh: And we got, like, 50 inbounds that [01:20:30] week because people

[01:20:30] Jess: heard.

[01:20:31] Josh: That's amazing. Yeah.

[01:20:31] Jess: Like, all these people heard I was gonna get asked to the dance. Exactly. And now they wanna ask me to the dance.

[01:20:36] Josh: I had, like, a, like, a Pretty Woman moment for sure. Yes. Oh. Huge mistake.

[01:20:41] Jess: Huge mistake. Huge. Big mistake. Huge. Okay, and then let's talk, what was week three?

[01:20:47] Josh: Okay, so-

[01:20:48] Jess: Or phase three, I

[01:20:49] Josh: guess. Y- yeah, so phase three was sort of like you ... Okay, we got through all of the, the practicing, then it was hitting the road. And so we hit the road with all of the people we had calls with in week two.

[01:20:59] Jess: Okay.

[01:20:59] Josh: And all of the, [01:21:00] the people that we had calls with in week three. And so now it's basically like, okay, we've narrowed it down to a pool of people that are showing interest.

[01:21:05] Josh: And you're, you're just hitting all of the cities. But the whole point or the whole goal is to make it look like you've got all this pull and all this traction. Yeah. And so I'd be like, "Yeah, I'm gonna be in New York on Tuesday, and I've got, like, one slot left." And I look at my calendar, and, like, I don't even have, like, a flight to New York.

[01:21:21] Josh: And I've got, like, no meetings that day. But so you're, like, playing this game.

[01:21:26] Jess: Yeah.

[01:21:26] Josh: And-

[01:21:27] Jess: Scarcity ...

[01:21:27] Josh: scarcity.

[01:21:28] Jess: Yes.

[01:21:28] Josh: Yep, supply and demand, [01:21:30] baby. And, and so you're playing this game, and eventually we hit the road. And we had some really good, good meetings, but eventually people start to drop out, right? They say, "Oh, we're not interested- Yep

[01:21:38] Josh: 'cause we just don't like, we don't like B2B. We don't like go-to-market. Like, we haven't seen a good outcome in this space for a while." And so you start to have this, like, existential crisis of, like, "Oh my God, like, have we spoken to enough people?" Yeah. Um, and, and yeah, I remember by the time I got to, I think, like, week four, which was my second week of, of travel, I think I was really only talking to, like, three serious [01:22:00] VCs at that point.

[01:22:01] Josh: Yeah. You're like, "Man, if the ... If these three drop out, we're starting all over again." Yep. And I remember there was a period of time, I think towards the end, end of January, where you kinda asked me, like, "How's it going?" And I was like, "This could be done next week. This could be four more months." Yeah. Like, like, it's so

[01:22:16] Josh: Who knows?

[01:22:17] Jess: So up in the air. Mm-hmm. And, but it could change tomorrow.

[01:22:19] Josh: Yes.

[01:22:19] Jess: It could change in an hour.

[01:22:21] Josh: Yep.

[01:22:22] Jess: Um, can I tell you from our side what all this was like?

[01:22:25] Josh: Yeah.

[01:22:26] Jess: Yes. Okay. So I think you did a really great job of preparing us 'cause you were like, "I'm literally [01:22:30] gonna have to step away from the business for at least a month, if not more."

[01:22:33] Jess: Yeah. And I think what it did for us was- We had to stop asking permission. Mm-hmm. Um, that's just something I've been, like, working on as a, like, as a professional, as a marketer in general. Yeah. And, like, it really gave me the ability to be like, "This is what Josh... If I think it's right, Josh will just want me to do this."

[01:22:55] Jess: Yep. "And he's not here, and I just have to make this decision." Huge. And I, and [01:23:00] I think all of the other team leads had to do that as well. It was really good for the executive leadership team to kind of have that, uh... It was like when you are in middle school and you, like, go on your bikes with your friends.

[01:23:13] Josh: Yeah.

[01:23:14] Jess: You know? And it's like you have the freedom to, like, go get ice cream.

[01:23:17] Josh: Wherever you wanna go.

[01:23:18] Jess: Like, we used to go to Farmer Jack and, like, bounce bouncy balls down the aisles.

[01:23:22] Josh: What the hell's Farmer Jack? It's

[01:23:23] Jess: a Michigan grocery store. Rest in power. I don't know. It's not here anymore.

[01:23:27] Josh: It's not around?

[01:23:28] Jess: No, it's so sad.

[01:23:29] Josh: Oh. [01:23:30]

[01:23:30] Jess: It was fun. You could just, like, go there, and, like, no one cared. Yeah. And that's probably why they're gone.

[01:23:35] Josh: Probably why they're gone. Anyway. Because they were selling bouncy balls.

[01:23:37] Jess: Oh, yeah. Yeah. Bouncy balls and groceries and stuff. And so you just, like, walk up and down the aisle. Anyway, like, that, that, right, that summer, that first summer that you had that kind of freedom-

[01:23:45] Josh: Yeah

[01:23:46] Jess: and you're like, "Oh, yeah, I'm kinda grown up, but I gotta be careful. With great power comes great responsibility." Yeah. Right? Yeah. And so it was kinda like that. It was like we, we have to be careful because we are still in the middle of the Series A raise, but we [01:24:00] also need to continue to grow the business while Josh is away.

[01:24:02] Jess: And so I think it gave us just, uh... It was like that, you know, coming of age summer for us, but it just happened to be in January.

[01:24:08] Josh: Was it... I feel like there's a, kinda, it's kind of a catch-22. If you ask any marketer right now, like, the thing that they want the most is, like, more control. Yeah. Like, "Hey, I've got strong opinions, but my leadership won't give me the budget.

[01:24:19] Josh: They won't give me the approval." Yep. So all of a sudden you had, like, free rein. Yeah. Was it- Mom

[01:24:22] Jess: and Dad are gone.

[01:24:23] Josh: Yeah. Was, like, the house party as fun as you thought it was going to be? Or what was it like?

[01:24:27] Jess: Uh, it w- it was pretty fun. [01:24:30] I'm not gonna lie. It was

[01:24:30] Josh: dope.

[01:24:31] Jess: It was pretty fun. But yeah, I think at the same time you have in the back of your head, like, "What would Josh say about this?

[01:24:36] Jess: How would he feel about this?" Yeah. "Is this the right thing? Is this what I should be investing in?" And, like, I think- Our entire team are, we're, we're very, like, mature. We've, we've done this before. This is not our first startup.

[01:24:49] Josh: Yeah.

[01:24:50] Jess: This is not our first leadership role usually for most of us. And so it was just kind of like, "No, we know what we're doing."

[01:24:56] Jess: And I think it actually gave us a lot of confidence to be like, "We do know what we're doing." Yep. We have [01:25:00] the trust, and we should just make the decisions we think are the right ones. I

[01:25:03] Josh: think you guys crushed it. Like, there wasn't a single decision that I came back to being like, "Oh, well, I would have done that differently."

[01:25:08] Josh: Yeah. The, the thing that I saw that was difficult was the cross-functional decision-making.

[01:25:14] Jess: Yes.

[01:25:15] Josh: Right? Yeah. Like, the, the glue being gone between the companies. Yeah. Or between the departments. Yeah. Which I almost feel like it's kinda good that it happened. It forced things to occur. It

[01:25:23] Jess: did, yeah. I think it made all of us, like, really

[01:25:26] Jess: We had to talk to each other. We couldn't go through you, which is a bad habit, right? [01:25:30] But, like, it happens, um, between the leadership team members and things like that. So yeah, no, it was, it was really good for everyone.

[01:25:36] Josh: Yeah.

[01:25:37] Jess: Can I read you a text message, a text exchange between you and I during this period of time?

[01:25:42] Josh: Oh, God, please don't.

[01:25:43] Jess: No, I'm going to.

[01:25:45] Josh: Shit. It

[01:25:45] Jess: doesn't matter what you want. I'm doing it. So this is dated Tuesday, January 27th.

[01:25:50] Josh: Okay, so this would be, like, the third or fourth week, like, the thick of- Yeah ... of me being in this process.

[01:25:54] You're,

[01:25:54] Jess: like, in it. Yeah. I haven't talked to you in a while.

[01:25:56] Josh: Yeah.

[01:25:57] Jess: I just want, like, a glimmer.

[01:25:58] Jess: Like, I wanna know, like, how it's going. Yeah. Is [01:26:00] this thing really gonna happen? How are you feeling?

[01:26:01] Josh: Yeah.

[01:26:02] Jess: So I say to you, "How are you? How'd today go? I feel like you're at war, and I'm waiting for a telegram." And you responded with this poetry. "Dear Jess, the battlefield was a scene to be held." "My morn started before the sun had kissed the sky.

[01:26:20] Jess: I'd presume 3:45 if I was so lucky as to have a time-telling machine." "I traveled thousands of miles to hold but two meetings. Urgently I found myself back in the [01:26:30] air, traveling yet again across our nation, alas, to New York. I arrive there tonight just before the clocks strike a new day, and with it bring a new journey, another two meetings.

[01:26:40] Jess: Have I met all the right associates to bring this nightmare to an end? I can only hope. I aspire the day we meet again to break bread, discuss the activities of marketing, record thy podcast, and get wasted in a Disney theme park." "Until then, I bid you adieu." [01:27:00] So I could tell your spirits were still up.

[01:27:02] Josh: That sums it up really well.

[01:27:06] Josh: I was sitting on a plane- ... literally crossing the country, uh, when you, when you sent me that text. And I think the journey was, like, so awful where I was just like, some creative liberty to, like- Yeah ... have some fun.

[01:27:21] Jess: Yeah. You needed that, I think.

[01:27:22] Josh: And I think I said that back to you within, like, minutes.

[01:27:24] Jess: Oh, it was so fast.

[01:27:26] Jess: It was like you had a degree in old English. I don't know wh- I, [01:27:30] I was, like, astonished at how well it was written and then how astonished at how quickly you wrote it.

[01:27:35] Josh: It just, it just flowed right out- Yeah ... of the mouth.

[01:27:38] Jess: It's so insane. Okay, let's talk about the monster you became.

[01:27:43] Josh: Yes, yes.

[01:27:44] Jess: The people are waiting for this part.

[01:27:46] Josh: Yes.

[01:27:47] Jess: When I say this, I say this with love. You're not a monster. I think what happened was, like, you were getting a lot of opinions thrown at you- Yeah ... of, like, what we should be, where we should be positioning ourselves, what we should be l- what we should look like in the [01:28:00] future.

[01:28:00] Josh: Yeah.

[01:28:00] Jess: And so you would come back, you know, on the one day that you were able to, like, come to us and talk to us between all these meetings- Yeah

[01:28:06] Jess: and be like, "Hey, I think we need to be an agency." And we were like, "O- O- Okay." You know? I think whenever your CEO comes to you with an idea, you're like that. You're y- The first inclination is like, "Where is this coming from?" "And how serious is he or she?"

[01:28:24] Josh: Yes. "

[01:28:24] Jess: And, like, do we really need to make this happen?

[01:28:26] Jess: And if it is in fact the case-"

[01:28:29] Josh: Yeah ... [01:28:30]

[01:28:30] Jess: how do we do that?" And so I think for the rest of us, it was kind of like we were trying to answer those questions. Yes. Like, how serious is this? What does this mean? What, how does ... This changes everything, right? And I

[01:28:41] Josh: wasn't around to help you. I think- No ... just so everyone knows, like, I literally would show up for, like, company all hands on, like, a Friday.

[01:28:47] Jess: Like, "Grenade. Agency." "We have

[01:28:50] Josh: 30 minutes. We need to become an agency." And, like, I'll, I'll explain, like, where these came from. But, like, to give people, I think, three themes or, like, three examples [01:29:00] of this. Yeah. There was, like, three back-to-back weeks where, like- Yep ... no one would see me. I would show up on, like, a Friday after traveling all week.

[01:29:05] Josh: And, like, week one, I would be like, "Great to see you guys. We need to become an agency. Goodbye." Yes. And then the next week was like, "Great to see you guys. Everyone should be concerned for their jobs because AI's gonna replace you. Goodbye." Yeah. And then there was, I think there was another, like, AI one as well or item.

[01:29:22] Josh: Yeah. Just, uh, awful.

[01:29:24] Jess: Yeah.

[01:29:24] Josh: Just awful.

[01:29:25] Jess: And yeah, I mean, I think, I think that was maybe, like, a byproduct of the series A raise that none [01:29:30] of us realized would happen. Yeah. That you would come back with all of these, like, opinions being thrown at you. Yeah. That you were like, "No, I need to throw this out and see where this lands."

[01:29:37] Josh: Yeah.

[01:29:38] Jess: But then, yeah, you would leave and we'd be like, "Hey, um, Alex, did you hear about this agency thing? Like, what, what does that mean?"

[01:29:43] Josh: Just complete turmoil.

[01:29:45] Jess: Like, existential-

[01:29:47] Josh: Complete turmoil ...

[01:29:47] Jess: business conversations without you.

[01:29:49] Josh: I made some mistakes- ... in that quarter.

[01:29:52] Jess: But I understand it, right? Like, you

[01:29:53] Jess: People are trying to decide if they wanna invest in you. And in- Yeah ... in doing that, they're giving [01:30:00] you from their experience and their perspective, like, what the future holds.

[01:30:03] Josh: Yeah.

[01:30:04] Jess: And you're trying to figure out where do we fit in that future?

[01:30:06] Josh: I think there are different kinds of founders, and there are pros and cons to each one of them.

[01:30:13] Josh: And what's funny is I think the thing that makes me like a, if I can toot my own horn, like a somewhat more enjoyable founder to work for is-

[01:30:20] Jess: Plus one

[01:30:21] Josh: Thank you. Thank you. I'll give you 20 bucks later. It's like, it's actually the thing that made me more malleable- Yeah ... uh, to come back with that, right?

[01:30:28] Josh: Like, I'm super [01:30:30] open-minded. Yes. I care a lot about people's opinions, right? And then you have these other sort of founders that are just like maniacal. They're like, "I work like 9:00-9:00, 6:00." Yeah. "We're building this thing. I know exactly what it is. Nothing you can say, no marketing idea- Right ... you could ever bring to me- Will change that

[01:30:43] Josh: is gonna sway- Yeah ... what I think about," right? And like, nobody likes the, no one likes to work for those founders. No. Yeah. Right? The reality is, is like there's actually some stability they br- bring because it's like so direct, right? On the flip side, like I went into these, this Series A process and you're, you are [01:31:00] talking to people that their only job is to talk to companies.

[01:31:04] Josh: Yeah. Like, that's what they do all day long. They

[01:31:05] Jess: see all the trends, all of the market fluctuations- Yep ... everything that's

[01:31:09] Josh: happening. They see, they see every sort of success story. Yep. They see every sort of failure pattern, right? And, and I'm super malleable. Like, I care a lot about, of people's opinions.

[01:31:17] Josh: And so, you know, they would sit down and they would say, "You know what? Like Sequoia just put out an article on how the next best companies aren't gonna be software. AI's killing the world-" Yep. "... and you actually wanna be a services company that delivers the outcome. You [01:31:30] can charge 10X more for it, and not get replaced by the, the AI models, but get enhanced, like when they get better."

[01:31:37] Josh: Yeah. And so I was like, "You're absolutely correct." Right? "We shouldn't build software anymore." And like I remember in one of our like Friday all hands, I like pulled up my screen and I had like written this like-

[01:31:50] Jess: Manifesto ...

[01:31:50] Josh: this manifesto. And it was so... Like if I still had hair, it was like emo, like hair-

[01:31:56] Josh: behind my ear, and it was just like, "I don't wanna build software anymore. [01:32:00] I wanna build outcomes."

[01:32:02] Jess: This is not a phase.

[01:32:04] Josh: This is not a phase. Dear Maria, count me in all time low. Um, and, and it just, yeah, it was just like, it was... I don't think these VCs were wrong- Right ... about like where the world was going, and I don't think I was necessarily wrong for like trying to figure out how we can fit- No

[01:32:19] Josh: ourselves into the narrative that would- That's

[01:32:21] Jess: your job.

[01:32:21] Josh: Yeah. Yeah. It was like what I needed to do to raise us money. I think I probably could've been a little bit wiser- ... towards like, there's difference between narrative and like, [01:32:30] "Let's go execute becoming an agency." So I'm sorry.

[01:32:33] Jess: That's okay. A- apology accepted from me, but you have to apologize to everyone else, so.

[01:32:38] Jess: No,

[01:32:38] Josh: fuck 'em.

[01:32:40] Jess: I can't be the only acceptor of all apologies.

[01:32:43] Josh: We should still become an agency.

[01:32:44] Jess: Josh, Josh, Josh, Josh, Josh. Do you know what time it is?

[01:32:46] Josh: Guess what day it is. Guess what day it is. What time is it, Jess?

[01:32:50] Jess: It is the time where we stare. Deeply, longingly, awkwardly

[01:32:55] Josh: Yep, right into the camera

[01:32:57] Jess: To the chagrin of many marketers.

[01:32:59] Jess: Right into that [01:33:00] camera

[01:33:00] Josh: And say-

[01:33:01] Jess: The things they need to hear

[01:33:03] Josh: Positive affirmations, baby

[01:33:04] Jess: For their hearts and their minds so that they can go on.

[01:33:08] Josh: Dear marketer, your CEO absolutely takes credit for the LinkedIn posts that you write for them

[01:33:15] Jess: Dear marketer, live, laugh, lower CAC. We have a happy ending.

[01:33:20] Josh: Yes.

[01:33:21] Jess: Thankfully.

[01:33:21] Josh: Yes. The company's bankrupt.

[01:33:23] Jess: We're going under. Every man for himself.

[01:33:27] Josh: No, we did it.

[01:33:28] Jess: We did it.

[01:33:29] Josh: We did it. We [01:33:30] raised ... We, we decided ... So we raised $10 million- Yep ... from SignalFire, a little tiny logo here. Yes. Let me get my SignalFire shirt on. Our original

[01:33:37] Jess: investor.

[01:33:38] Josh: Our original investors, which we should talk about that- Yeah

[01:33:40] Josh: because that was interesting. So we raised $10 million from SignalFire, one of our original seed investors. Uh, and a big one, which was HubSpot Ventures- Eee ... invested in us, which was massive. So we should talk about sort of like why we got to this outcome. Yeah. Like why 10 million? Why did we pick these partners?

[01:33:56] Josh: And sort of like what does that mean for us? Um, so 10 million is [01:34:00] a ton of money, but also, like small- Yeah ... in consideration to the rounds we're seeing every day- Totally ... on LinkedIn, and that was very purposeful- Yeah ... for us. Um, what people don't see on the other side of the LinkedIn post of like, "We raised all this money," is you're actually diluting the company.

[01:34:15] Josh: Yep. So for those people that don't know, like when, when you raise money, you're adding new shares to the pool, right? So that means that like the pool is bigger, which means your percentage of shares are now a smaller percentage of that pool. Yep. So the more [01:34:30] money you raise, the more you actually hurt the existing shareholders, i.e.

[01:34:33] Josh: our employees. Yep. So we wanted to raise enough money that would answer the things we talked about at the beginning of the episode, which was like security, opportunity to like go build the right product to capture the, the market and then the opportunities that were in it, but also not so much that we- Yeah

[01:34:46] Josh: you know, just had like a silly amount of money that everyone was diluted. Yeah. So 10 was the right number for us. We did all the math. What was your, what was your trademark? Big, big, uh-

[01:34:55] Jess: Oh, it was a deep ass financial dive.

[01:34:57] Josh: Deep, we did- TM ... a deep ass financial dive, [01:35:00] TM. Um, and that was the number for us, where it's like we can build a really big business, get to profitability if we wanted to- Yeah

[01:35:06] Josh: raise more money if we wanted to. Like it gave us a lot of optionality. So that was the right, right number. Um, SignalFire coming into the round was like a really interesting sign to the market- Yeah ... because they like knew everything about

[01:35:17] Jess: us. They know ... They've seen all our dirty laundry, right? Yeah. They kinda know all the good, bad, ugly, everything.

[01:35:22] Josh: Mm-hmm, they saw-

[01:35:23] Jess: And still wanted a piece of the

[01:35:23] pie.

[01:35:23] Josh: And they still wanted a piece of the pie. Yeah. They just, they got it, right? Yeah. They, they understood sort of our vision. They [01:35:30] understood that like nothing's being built for marketers right now, whether it's ad targeting, whether it's site de-anonymization.

[01:35:36] Josh: There's like all these things that like sort of Vector's been known for, and we're- Yeah ... you know, still in the journey of like sussing out exactly where we take the, the product in the future. But they just sort of believed in what we believed in, which is like marketers in the age of AI are being ignored, and like we're the only company that's really set out to try to make them superhuman.

[01:35:54] Josh: Yes. And they just got that. And the fact that they understood that despite seeing all of our dirty laundry, I was like, "That's the kind of partner- [01:36:00] Yes ... that we want."

[01:36:01] Jess: Love that.

[01:36:01] Josh: And then we got HubSpot.

[01:36:02] Jess: HubSpot.

[01:36:03] Josh: Which was- Big

[01:36:04] Jess: I remember when you first told me, and I was, like, losing my mind.

[01:36:07] Josh: Yeah, yeah.

[01:36:08] Jess: Because, I don't know, a series A is very exciting.

[01:36:11] Jess: Mm-hmm. Again, like, the, the ability to go to announce that, it's, like, instant credibility, instant legitimacy, right? Yeah. But then to put a name like HubSpot behind that-

[01:36:19] Josh: Yeah ... whew,

[01:36:20] Jess: that was, that, for me, was like, "Oh, man, this is, this is gonna be good for us." Yeah. "This is gonna be so big."

[01:36:26] Josh: The DNA was just so perfect.

[01:36:27] Josh: Yeah. We're a Boston-based company. They're [01:36:30] Boston, right? Founders and some of our early team came from Drift- Yep ... which, you know, spun out of David Cancel, which, um, was the chief product officer at HubSpot for a long time. Yeah. Like, it just made a lot of sense. Yeah. Um, like you said, the credibility was, was great, and then also just, like, their ability to help us deliver more for our customers, right?

[01:36:47] Josh: Yes. The, they've got, like, a great partner network. Like, we're gonna build, like, deeper embedded apps that, like, we otherwise could not build- Yep ... without them. Just, like, really cool stuff that we can do now.

[01:36:55] Jess: Yeah, 100%. I think they get what we're going for, too, which is, like- [01:37:00] The, the contact level, seeing the humans that are showing up on your site, understanding how to market to individuals in a way-

[01:37:07] Josh: Yeah

[01:37:07] Jess: that, you know, you hadn't, you, you did not have the ability to do before.

[01:37:12] Josh: Yeah.

[01:37:12] Jess: And I think that is their feeling as well. Yeah. Like, they, they really understand the idea of just, like, giving marketers more powers- Yeah ... superpowers. And, uh, yeah, it just is such a nice- So good ... such a nice fit.

[01:37:24] Josh: I think, um, one of the things that really attracted me to HubSpot, beyond everything that you just described, is, like, HubSpot's done such a good job of [01:37:30] predicting where the marketing world was gonna go.

[01:37:32] Josh: Yeah. Yeah. Right? From, from inbound to now they're unbound. Yep. And, and just they've done such a good job of, like, understanding categorically where shifts are gonna go. Yeah. And, like, ultimately, that's what we want Vector to do, which is, like, predict where marketing's going to go for our customers.

[01:37:46] Jess: 100%. Uh, we also did a really fun thing where...

[01:37:50] Jess: It's funny, we're recording this today.

[01:37:52] Josh: Yeah.

[01:37:52] Jess: We're actually announcing this in real life- Yeah ... in, like, real time-space continuum-

[01:37:57] Josh: Yep ...

[01:37:57] Jess: tomorrow.

[01:37:58] Josh: Yeah.

[01:37:58] Jess: By the time this comes out, it [01:38:00] will have been announced. Yep. And so we put together this really fun video-

[01:38:04] Josh: Yes ...

[01:38:05] Jess: uh, where we all, you know, everyone who wanted to be a part of it got to be a part of it, and it felt like this, like, um, it was almost like a, the opening theme to, like, a '90s sitcom.

[01:38:15] Josh: Yes.

[01:38:16] Jess: And we filmed in Boston. We were all there, uh, celebrating the series A raise. Yep. And yeah, so, like, that was a really fun experience, too, where everyone kind of got to be a part of this celebration and the announcement. And so we did, we're gonna, we are going to do [01:38:30] by the time this is out, we will have done- Mm-hmm

[01:38:31] Jess: um, like, a two-part announcement, right? Where it's, like, your typical kind of the image that goes up on, uh, LinkedIn, the press release, the blog post. Yep. HubSpot and SignifAI are kind of doing their own distribution of it as well, and then we're gonna drop this video. And I feel like people are gonna be like, "These people are just-

[01:38:48] Josh: Unhinged

[01:38:49] Jess: nuts." And we love it.

[01:38:52] Josh: So, so speaking of which, right? So you came up with this video concept. Like, once we raised the money, I came to you and said, like, "Okay, what now?" Yeah. [01:39:00] How did you think about, like, announcing, press releases- Yeah ... not, et cetera.

[01:39:04] Jess: How do we get this out to the world?

[01:39:05] Josh: Yeah.

[01:39:05] Jess: How do we distribute this news?

[01:39:06] Jess: Mm-hmm. So typically, you know, you ra- you fundraise, and the first thing you have to think about is, like, the, the press release, right? The pitch. How are we actually going to pitch this to anyone who cares who might distribute it? And we went down that road for a while, and, uh, we just kinda kept hitting blockers- Yeah

[01:39:24] Jess: of, like, hey- We get that, like, HubSpot invested. We get that you're trying to do this really [01:39:30] cool thing and, like, give marketers superpowers, but, like, press doesn't care.

[01:39:33] Josh: Yeah.

[01:39:34] Jess: And I remember I came to you at one point, and I was like, "Do I... How, how far do you want me to take this PR thing?" Yeah. Because we could we- weave a story that we're all kind of mutually dissatisfied with-

[01:39:44] Josh: Mm-hmm

[01:39:45] Jess: uh, to get into some press, or we could just do our own thing. Yeah. And we could, like, go, you know, do this video. Yeah. We can all post on LinkedIn. I'm sure that, like, Signifier and HubSpot will support us. They'll do the distribution- Yeah ... on their end. Maybe [01:40:00] that's enough. Mm-hmm. And you were like, "Yeah, let's just go that route."

[01:40:02] Josh: Yeah. I, I think it's funny because the, the press release story almost brings me back to the fundraising story. Yeah. Which is, like, we-

[01:40:09] Jess: Yes ...

[01:40:10] Josh: we kinda realized there was, like, theater, right? There was all these things that we were doing for the wrong reasons. Yeah. Right? Like, we had to, like, get our, you know, the, the story in, in, like, an optically good s- place to raise.

[01:40:24] Josh: Then I, like, came to you guys and was like, "We should be an agency," because, like, optically, that's where, like, everyone was. Yeah. And then, like, the [01:40:30] press release was like, "Well, in order to get into TechCrunch, you need to tell this story." And we kinda realized, like, none of this matters. Yeah. Like, we raised this money because we wanted to build a good product for, like, our customers.

[01:40:40] Josh: Yeah. And, like, we were just so over the theater-

[01:40:43] Jess: Yeah ...

[01:40:43] Josh: at that point. We're like, "Let's just get back to, like, building our business."

[01:40:46] Jess: Yeah. Let's just tell people. I think the fact that, like, HubSpot's a part of it, uh- Yeah ... i- is, is plenty to get the people we need to be excited about it excited about it.

[01:40:55] Josh: Yeah.

[01:40:56] Josh: I, I remember, if we can be tactical real quick. Yeah. There was, yeah, [01:41:00] um, w- now that we had partners, we had people at Signifier, we had people at HubSpot. Yep. I had an opinion. You had an opinion, right? And that was part of, and then obviously the, the- They

[01:41:07] Jess: had an opinion, yeah ... you know, the

[01:41:07] Josh: press release folks, yeah, the, the, the reporters had an opinion on, like, what would get picked up.

[01:41:11] Josh: So everyone had their opinion. One of the things that... Or the story that you and I wanted to tell was essentially like, hey, like, what Vector really believes, and ultimately, like, all the BS aside, what we believe in is that, like, marketers as humans are really important. Yes. They have taste. They're not going to get replaced.

[01:41:28] Josh: And we want to [01:41:30] build AI tools and platforms and all, all of this, but ultimately, it's because, like, we wanna build for them.

[01:41:34] Jess: Yes.

[01:41:35] Josh: And, like, one of the pieces of valid feedback we got was like, "Oh, well, the sort of AI not replacing humans is, like, a really played out, like, trope."

[01:41:43] Jess: Yeah.

[01:41:44] Josh: And we were like-

[01:41:45] Jess: Yeah, but not in our world.

[01:41:46] Josh: Yeah, not in our world.

[01:41:46] Jess: Right?

[01:41:47] Josh: Like- And also, but it's our truth. Yeah. Like, that's, like, maybe it won't get picked up by TechCrunch, but, like, that's what we're building.

[01:41:53] Jess: Yeah. E- every day I go to LinkedIn, and it's like, "I replaced my 27-person marketing team with one bot."

[01:41:59] Josh: Yeah. You

[01:41:59] Jess: know?

[01:41:59] Josh: It's- That [01:42:00] guy sucks, by the way

[01:42:00] Josh: that,

[01:42:00] Jess: he's the worst. Yeah. He is many.

[01:42:03] Josh: Yeah.

[01:42:03] Jess: He is many. But he is, he is out there. But

[01:42:05] Josh: he sucks.

[01:42:05] Jess: He really sucks. So yeah, it's like it is still part of our truth. It is still happening. Like, yes, maybe the news cycle has passed. Sure. But that doesn't mean the story has ended there.

[01:42:13] Josh: Exactly.

[01:42:13] Jess: Right?

[01:42:14] Josh: Yeah.

[01:42:14] Jess: I mean, Josh, now we have all this money.

[01:42:16] Jess: Like, I'm just gonna throw an idea out there, and you just, like, give me back whatever comes to your mind. Okay. Yeah. Like real ghosts, like real ghosts.

[01:42:23] Josh: Like, like spend the money on like getting real ghosts Like,

[01:42:26] Jess: make them or find them.

[01:42:28] Josh: Jess, I have enough money to still fire you. [01:42:30] I just want you to know that.

[01:42:31] Josh: But this was a great meeting.

[01:42:32] Jess: I'll workshop it some more. This was a good meeting.

[01:42:34] Josh: This meeting could've been a podcast.

[01:42:35] Jess: It could have.

[01:42:36] Josh: It was. It

[01:42:37] Jess: was. This Meeting Could Have Been a Podcast is a Vector production. Vector lets you build ad audiences from real people that visit your site, click your ads, and research your competitors.

[01:42:47] Jess: Imagine seeing exactly who will see your ads by name before you spend a dime. It's a great time to be alive, marketers. Go give it a whirl at vector.co. See you next time.