The Transaction

TT - 066 - Rachel Dines
===

Rachel Dines: [00:00:00] Focus in the Go-To-Market side is always the greatest

Achilles heel of so many startups.

A lot of startups I'm talking to lately have way too many use cases and way too many target segments, and they

think they can attack all of them all at the same time

The flexibility is a trap.

If you are just starting a relationship with the analyst, when you sign your contract, you're behind already.

We're coming up with our short list. Who are the top two or three analysts who we need to have strong relationship with,

who might be writing the magic

quadrant or the wave or whatever?

And who are we going to go after now?

It's wild how fast

you can get to market now with AI tools.

Because of AI companies are actually getting to customer facing product much faster than they ever were before.

They're vibe coding their way into a product in a couple of months and they've not had enough time to really bake in the Go-To-Market strategy.

People are hiring heads of marketing way too early. And your

first marketer should be a product marketer,

Craig Rosenberg: I've always loved the term masshole. It's just

one of my favorite things.

Rachel Dines: I, I embrace

it wholeheartedly. Like I, I,

grew up in Massachusetts. I've lived [00:01:00] most of my adult life in Massachusetts. I did live in San Francisco for a little while, and um, that's when my most masshole-y nature came out.

Um, when I

lived in the Bay Area. Yeah,

I don't know. It's just, I missed it, I guess us.

Matt Amundson: well, you know.

Craig Rosenberg: Our, yeah.

Matt Amundson: Folks from, from from Massachusetts. A little bit more straightforward, uh, here in California. We like to talk shit behind people's backs

Rachel Dines: There you go. Yeah. We we're at least mean to your face. Like if, if I think something Yeah, I'm

I'm just gonna say

Matt Amundson: and I, I appreciate that, even though I, I can't demonstrate it as a quality for myself, but I appreciate

Craig Rosenberg: I can't damnit. By the way, are New Hampshire people, red Sox, like fans? Is

that

Rachel Dines: Yes. Yeah. New Hampshire's in Red Sox

Nation.

Sam Guertin: Oh

yeah.

Craig Rosenberg: Okay. All

Matt Amundson: All right. Um, okay.

Craig Rosenberg: what was that bad, Matt, your

Matt Amundson: I think that that was a fair question. I just gotta make sure I don't have any Yankees paraphernalia around me

Craig Rosenberg: Are you a Yankees fan on the side?

Matt Amundson: on the side. Yeah. So Dodgers number one. Yankees [00:02:00] number two. It's a, it's a family thing. It, you know, uh, it's probably not worth exploring on this pod.

Rachel Dines: let's not.

Craig Rosenberg: I will say that those are intriguing choices.

Matt Amundson: Yeah, well, I grew up in LA and so I mean, it was all Dodgers. All Lakers.

Craig Rosenberg: Yeah, that's why, why did you Well, I mean, adding the Yankees

Matt Amundson: okay. All right. So yeah. Yeah.

Craig Rosenberg: Rachel, but yeah. Um, all right. So, um, so Rachel, you want to know how, uh, how we like to have fun? We hit record like two minutes ago, so we were recording Massell

because

Matt Amundson: are like a, yeah,

we're like a cold, open.

Craig Rosenberg: what

Rachel Dines: I I.

clocked that on the podcast recording thing. Um, And also not my first rodeo.

Friends. I'm,

Matt Amundson: Whoa.

Craig Rosenberg: Whoa.

Wow. Look at This, mass hole in effect. God, I love this. No, it's don't, do not apologize

[00:03:00] that Sam, please cut the sorry out and leave

everything

Matt Amundson: Yeah.

Craig Rosenberg: you. Um, ​

so here's how we got here Today. It's, we are just talking about how I think we scheduled this like months ago. Um, and, uh, but I, I met you through Scott Mersy and, um, he was like, dude, you gotta, you gotta meet Rachel. Um, she's like the, one of the best that I've ever worked with, especially with early stage, which is a really interesting and difficult, challenging, you know, area. Matt is like also a masochist. He [00:04:00] does early stage CM

Oing, which is like, yeah, you, yeah. He throws

himself out there. Yeah. Um, so that, and then when I met you, you were, um, you weren't a mass, well you were, I guess. I mean, technically like, um, by location you were, but you, high energy, uh, doing really interesting things and a topic we had, you know, like product marketing, Go-To-Market strategy on the marketing side for early stage. Uh, we haven't really had that conversation, so I thought it would be amazing to have you on the show and that's why you're here today.

So welcome to

The Transaction.

Rachel Dines: Thank you. I'm excited to be here. Um, I'm actually, I'm gunning for the Sam McKenna Award, so,

uh, hopefully we'll make it a good,

we'll have a good conversation. Um, yeah,

I shoot. Hi. Uh, but didn't

didn't you on the Sam McKenna thing, didn't you guys talk about having an award for like, having her be the best

guest? I was like, I can do [00:05:00] better.

Craig Rosenberg: oh, I

Matt Amundson: To challenge accepted. I like it.

Craig Rosenberg: dang it.

Rachel Dines: no, but that was a really good episode. I, um, I, you

know, I have to admit, I only started listening when I met you, Craig, back a couple months ago, but then now I'm hooked and I, it's weird because I feel like I know you both really well and you don't know me at all. So it's a very, we're having like a strange parasocial relationship moment.

Craig Rosenberg: Yeah, no, this is really, this happens to people all the time and so we really appreciate that. Um, but actually, if you don't mind for, for this one, I, I introed you, as you know, that's our classic intro, but for the audience, you wanna do like a minute on, on you and, and your background just a little bit. We don't normally do this, but I think it's appropriate here.

Rachel Dines: No, I think it's good.

'cause I'm, who am I? I'm a nobody. So, um,

I've actually, well, I've been out, I've been flying under the radar for a bit. And

Craig Rosenberg: There you go. Thank you. You're

marking, flying under the radar is different than you know. Yes.

Thank you. Much better branding. Yeah. so,

Rachel Dines: uh, I started my career, uh, as an industry [00:06:00] analyst and I was at Forrester, uh, covering, well, I started out covering like data center facilities because nobody else would cover that. It was

like the most boring thing. And they're like, you wanna be an analyst? You get data center facilities.

And I was like, let's do this. Power cooling, fire suppression, like. I can get excited about that.

Um, and slowly over time, I mean, honestly,

actually I can. Um, but uh, over time, uh, I

got a chance to cover a couple diff different things at Forrester. I remember last time, Craig, we were geeking out about being ex analysts,

um, last time we talked,

uh,

and I eventually ended up in storage and

then this weird bookstore came around. Saying we've got a storage solution. It's cloud, it's S3,

it's am, it was Amazon. So, um, that I was lucky enough to be at Forrester at the dawn of cloud and got to cover early early cloud and then jumped over to the vendor side and worked in cloud storage at some big tech at Riverbed, at NetApp. Then I did small tech and that's when I really got the bug to do, to do [00:07:00] startups.

And then in the past, for the past 10 years, I've been doing early stage startups.

At CloudHealth through the acquisition of VMware. Then most recently at K Chronosphere, four years, amazing time. Learned a lot. Decided I wanted to just go basically freelance, independent. Um, and now I'm, I'm working with a whole bunch of different companies, um, and working on my novel. So that's, that's my life these

Craig Rosenberg: these days.

That's amazing.

A Quick Convo about Data Centers & The Mission Impossible Film Franchise
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Craig Rosenberg: By the way, speaking of data center cooling, if you guys don't mind, last night I watched the Mission Impossible, where he dives into that. Water to get the thing out. It's an incredible scene. Was that a data center underwater? What

Rachel Dines: It

was, it

was, and that's a real thing.

Um, so yes, it's a real thing.

If you go, so around 2010, I think it was, Microsoft started putting data centers underwater because the most expensive thing about data centers. Do you know what it is?

Matt Amundson: the cooling.

Rachel Dines: The cooling. Right. And so where, how, what's, what's really cheap, easy

way to cool

something.

Craig Rosenberg: something.

Rachel Dines: Ocean [00:08:00] Water.

Ocean, water. Right. Thanks, Matt. You're So

Craig Rosenberg: excited in your

answers. Yeah, I'm like, I this is great.

Rachel Dines: Um, uh, so I mean, okay, I

wasn't gonna bring this up, but I'm just, just 'cause you

mentioned the underwater data centers,

it's what gave me the idea for the concept for a data center on the moon.

And That's what my novel

Craig Rosenberg: novel is about. No way.

Rachel Dines: Yeah.

Craig Rosenberg: All right. All right.

Rachel Dines: So anyhow, full, there's the full

spectrum of industry analysts to early stage. Oh, and I

should have said, I, and at all

of those companies, you know, NetApp, Riverbed, Kronos, we Cloud Health. I was a

product, I'm a product

marketer. that's

really my, that's my jam. That's my focus.

Um, and, and yeah, so

even when I was like first marketer in the door,

like I was at Chronosphere, I, I was a pro product marketer.

That's, I know enough to be dangerous in the other areas, but that, that's my focus area.

Matt Amundson: Love it. Love it.

Craig Rosenberg: You We had say? High energy.

Matt, what do you think of Rachel's energy level on a scale of one to five? Five being extremely energetic,

one [00:09:00] being not energetic. Oh no. Do I need to, to turn it down? Do I turn

Turn it down. No. No.

no. That was my point. That was my point. Sometimes when we have new guests, we get a little freaked out.

They, they don't know how to handle us. They did not do their pre-work. And this has been awesome so far, including you going with the Ethan Hunt, understanding my Ethan Hunt call. So, sorry,

Matt Amundson: Can we break down any other Mission Impossible films? Um, let's talk Burge Khalifa. Do we think that that was a viable No. We, we

Craig Rosenberg: Wait, I'm gonna

say this.

Rachel Dines: Yeah. Oh no, I was just gonna, I actually used to use the GIF from Mission Impossible in like my, some of my Forester presentations, like the GIF of it from the very first one where he belays down from the ceiling to

like tap on the, like to hack into the mainframe. I used to use that in my presentations all the time.

Matt Amundson: Nice. Nice.

Rachel Dines: Yeah.

Craig Rosenberg: That's amazing. So let's, let's get going even though we're having fun already. So, ski, uh, Matt gives you, oh, wait, wait. Matt, were you gonna, um, ask a question by the way, when I [00:10:00] interrupted?

No

Matt Amundson: No.

Craig Rosenberg: you weren't. Okay. Um, so we got, uh, as you know, there's sort, there's two big questions on the show. One is like we ask you to tell a story, uh, amazing Go-To-Market story. Um, and then two, we talk about like, you know, the one to three things you're seeing that work today. And we're really, uh, from a product marketing perspective will be fascinating. Um,

Marker
---

Craig Rosenberg: so on the story and your desire to beat Sam McKenna, let's hear what you got. What do you got for us?

Rachel Dines: Okay. I don't know if I can beat Sam's story 'cause that was good. I, I thought about this a bit.

Um, okay, so I'm gonna tell a story. I'm not gonna name names. And I also think the statute of limitations on this

has passed 'cause it's now been like

15 plus years.

Um, so I wanna tell you the story. Yeah, I wanna, it's vintage

and it's just such a good one.

And just before I say it,

the person, this story is about amazing person. They were a mentor to

me. I, he very much respect them. But this is gonna be a little bit embarrassing to them, so I'm not gonna say who it

was. Um, [00:11:00] this is the

story of how I gave my very first solo,

like main stage presentation at a conference. Um, I believe it or not,

was a shy child.

I was not extremely

out. Okay.

Well, I was a little bit shy. I was scared of,

I was scared

of giving presentations. Like I

did not, like public speaking. I, it was not my jam. Um, and so I was at Forrester, you have to be able to give talks. You have to give speeches.

That's a big part of being an analyst. And so I was gearing up for my very first presentation

at a

Forester conference. And, um, it was

a co-presentation, so it was like, okay, I'm not on my own. I've got a co-presenter. I can do this. But I was the more junior person. So basically I did all the heavy lifting.

I built the slides, I built the talk track, I built the whole presentation. There was a whole back and forth and banter. It was gonna be a great two person presentation at a Forester conference in Las Vegas at 9:00 AM on the last day of the

conference.

Matt Amundson: Which, uh, which expo hall, which conference center.

Rachel Dines: Uh, it was at the

Venetian. [00:12:00] Okay. Yeah, that's a good one. I like that one. Mm-hmm.

I've spent way too many nights at the Venetian, like the smell of it. Just when you walk in the smell, that's the, the international flavors and fragrances smell that they've pumped through the air. Anyhow,

it just makes me feel nauseous. Um, so, uh, so of course the presentations at 9:00 AM so I'm up at five.

I'm practicing

rehearsing. I get there, I get there an hour early. I scope out the room. Everything's good. We're 45 minutes out. My co-presenter is not there. We're 30 minutes out. My co-presenter iss not there, we're 10 minutes out. My co-presenter iss not there. About four minutes out the room's already filled up. My co-presenter, shuffles in sunglasses on a little disheveled, sits down in the front row, puts lean's back, puts their feet up on the chair in front of them and says, I think you got this one solo.

Matt Amundson: Oh.

Craig Rosenberg: No way. Thank you.[00:13:00]

Oh, look,

Rachel Dines: uh,

so I was, I was like,

I don't got this solo. I need you. And he was like,

I'm not

in a state to be presenting right

now. You know, this

stuff cold. You got this, I

believe in you.

I'm here

And he was like, but I'm not here to present. I'm here to be for support you.

And so that was, um,

so I'd like to say I got up there and I crushed it.

Um,

I don't, but honestly I don't remember at all. Like, I think I like blacked out. I got to the end,

people. said, I mean, I didn't like, you know,

completely shit the bed. I'm sorry. We, I don't, are we allowed to swear? I

didn't completely

Craig Rosenberg: We

encourage it. Yeah.

Rachel Dines: it out. Okay. I didn't completely shit the bed. I don't think it was that great. But, uh, I survived and at the end he was like, see, I knew you could do it. You didn't need me. And I was like,

you, I'm going to kill you.

Matt Amundson: There is something, there is something so crazy about presenting in front of a big audience like that. You do leave your body, you absolutely leave your body. You're just like hovering above, looking down [00:14:00] at yourself, presenting and just

going like, oh my God. Like, what's on the next slide? What's on the next slide?

What's, I can't remember what comes next?

Rachel Dines: And you, I get into like a fugue state too, where I'm just going and like luckily if, if I've done it right,

I've rehearsed it a few times, so I don't need to worry about the timing. And I just like, I'm, I just go.

But yeah, this, I mean this was my very first one.

Uh, so that kind of got me over my fear of presenting, um, in front of large audiences and, and giving webinars and, you know, giving big talks because I was like, okay, bye.

Could do that. I can,

I can do

whatever I need to do Uh, so

yeah, that's, I don't know.

Craig Rosenberg: I dunno.

That was a

that was

a great story. Are you fucking kidding?

Matt Amundson: Yeah.

Craig Rosenberg: did you watch the show, the studio?

Rachel Dines: No.

Do I Oh,

Craig Rosenberg: No. Yeah,

Matt Amundson: Yeah, I think you should.

Craig Rosenberg: the studio has a very similar situation, um, to, to what you just, uh, what you just described.

Um, that was, that was a great story. Um, also, I. I [00:15:00] believe that there's a guy in a, in a full red outfit in behind us,

Matt Amundson: Yeah.

Craig Rosenberg: things. Yeah,

Rachel Dines: I know,

uh,

yeah, that's my husband just wandering

in and out of the screen because, um, that's what he does when I'm on podcast. Like, I, have you seen, I was on the, um, and my son's probably about to come join me because they just can't leave me alone. I told 'em I just need an hour alone.

Uh. Um, I was on, um, do you know Corey Quinn?

I was on last week in AWS

like his podcast, which is a pretty big one, and my husband just walked back and forth like four times. I'm like, guy, I just need an

hour. Like,

can you just leave me alone? me

too much. I'm

Craig Rosenberg: it's too hard. Hey.

Yeah. I like it. I like it. All right. So, um, that was a great, that was so well done.

Matt Amundson: We love that You're still,

Craig Rosenberg: you're still tracking. Great.

Okay.

So here, here's the meet. We just kind of, you get us going and then we will ask, uh, as we go and, and see where the conversation goes. But like, um, I'll give you a little context, which is, you know, Matt and I started the show because we were [00:16:00] constantly just trying to figure out like what's working today and what's not, because things were changing so fast. And then we were just having fun doing it, and we were like, let's just make a podcast. And so that, you know, it's fun for us to do. Uh, and we also wanna learn,

Why Startups Need To Engage The Industry Analysts Early On
---

Craig Rosenberg: so the big question we ask is like, what are the like one to three things you feel like, uh, work in today's environment and, uh, you know, you know, give us examples and, and, and, and we'll dig in on kind of what it looks like.

And we're looking forward to hearing what you have to say there.

Rachel Dines: Yeah, no, and um, it's such a good question and I agree with, with what you've been saying recently that things are changing

so fast right now. Like I've not seen the speed of change

in like the 20 or

so years I've been in

basically

all, all only in B2B like SaaS since it was invented deep tech and all of a sudden things are changing faster than ever. Here's one thing though, that's not changing.

[00:17:00] And

it's industry analysts and the need

to engage with that. Yeah,

It's, I can't not,

it, it's,

and it's not just because I was an industry analyst, but I've worked with so many companies,

so many startups on their analyst strategy, and they, all of them seem to make the same mistake, which is not engaging early enough and not taking it seriously enough. I think a lot of

companies are like,

uh, we'll just do Gartner later. We're

not big enough. We're too small.

We'll do Forrester later. We're too small. There is a point where you're too small to buy a subscription,

but I Don't think there's

ever a point when you're too small to have a relationship and start building that because it's a long game.

It's a

Matt Amundson: Yeah. long game.

So you recommend, even for people that are not ready to sign up for a subscription to either Forrester or Gartner, you know, go out. Try to schedule some time with an analyst, get to know them, you know, start to seed your story in early, um, and just start to build a relationship. And then [00:18:00] as you become a customer of theirs, that's when you know, then you're not building from the time that you've already started.

You're contract you're building before then.

Rachel Dines: Exactly. If you

are just

starting a relationship with the analyst, when you sign your

contract,

you're behind

already. Right? You should have

one to two years of relationship building. I think a lot of people really feel are a little disillusioned by

the analyst and feel like they're really pay for play and

like, oh, you can't get anywhere without

paying. And

like, at

least for Forrester and Gartner, I promise that is really not true. Like they are so separate from the commercial, and I'm not to throw the other ones under the

bus, I just don't have as much

personal

experience with the other

ones. But like there's, the analysts are so commercially separate from the

commercial

agreements. They're interested in exciting new tech. People sometimes say like oh, the analysts are always behind the

times. That's because the new exciting vendors aren't talking to them,

aren't taking the time.

to talk to them. And

I think

this has been true forever. Like when I was

an analyst, um, and I, you know, I was cover, I had, I was, man, I covered a bunch of different [00:19:00] things, but like I was covering the hyper-converged space and there was this little startup with like four people called Actifio and the CEO used to come visit me and bring me tiramisu because he knew I loved tiramisu.

And we would just eat tiramisu and chat and like, yes, I can be bought for tiramisu

Matt Amundson: was gonna say that really flies in the face of your pay-to-play argument, but

Rachel Dines: But it was more about the chat and the relationship,

right? And like, and the fact that he remembered that that was something that I liked.

Um, and like flying forward to, you know, today, if I look back at the startups that I've worked with and I've advised, usually we start the analyst relationship. We do briefings.

We have, we meet at conferences like you can't do, there's certain things you can't do without a paid relationship, but there's lots that you can,

um, and. That's just gonna pave the way to actually getting something out of it in the many years later.

Um, so even like, I, I'm working with a company now that's just about to come outta [00:20:00] stealth and, uh, we're, we're already, we're, we're going to analysts right away.

Um, they're not gonna

probably buy a subscription for a couple years, but they're, they're already we're, we're coming up with our short list. Who are the top two or three analysts who we need to have strong relationship with, who might be writing the magic

quadrant or the wave or whatever? And who are we going to go after now?

Craig Rosenberg: Okay,

so, but what is, like, what, like, so that's,

Marker
---

Craig Rosenberg: you're with a seed company and you're doing this, but what do you do? Like you, so I'm a, you know, I'm a young, mostly founders at

that point, and so they. Uh, so you feel, is it Gartner Forrester, uh, independent analyst? Like do you map the analyst world then when you say go to them, like what, what do you recommend?

How do you recommend people approach this?

Rachel Dines: So

usually

we'll start, do our research and make a list, right? Who are

the 15 to 20

analysts in our space

who might be relevant and we might be able to form a relationship with. And those PE analysts are gonna cover from [00:21:00] Gartner to IDC, to forestry, to lots of independents.

And the

independents and the boutique firms are really, can be the lifeblood for, for, uh, startups especially.

As you're just getting started and like maybe a forester gardener doesn't want to talk to you or you can't get traction with them, that's

fine. You can get a lot from the boutiques. So you make your list,

right?

And then you have, you need to have some meaty news to come to them with. Right. So with this particular seed stage company that I'm working with, we're gonna come to them with the, um, a

pre-brief on their launch.

On their coming, on their coming out party, basically.

Right. And we're going to set up 30 to 45 minute

briefings for each of these analysts, and we're working

on,

Um, you know, like we tell them the whole story, not just the tech, but also like the business and the founding and the customers and the, you know, like they like a really holistic story.

We can talk about that more in depth.

Um, and then from there we'll see like who are we getting traction with? Like, which of the analysts are really

nodding along and saying like, oh

yeah,

like this, I get this. And which we're like, yeah, whatever.[00:22:00]

And we'll probably narrow it down to like two or three analysts from there that we think we can actually have bought in our vision

and we can start to build a relationship with.

And from there, it just goes into a

cadence of, you know, every

six months

making sure we're touching them, um, like live

and

then every month even touching them virtually with an email or, or on social and things like that. And it's just kind of like a little playbook that you go through.

Matt Amundson: Interesting. Interesting. So when you talk about like, uh, keeping in touch with them, like via email, do you think of things like, almost like a repeatable newsletter? Like here's what's new, here's what's we launched, like here's the type of customers we're adding, here's the use cases that we're solving for.

Like how would you structure something like that?

Rachel Dines: So usually in the beginning, I keep it really casual. It's not like a big formal newsletter. It would just

be

like, You know, Hey Craig, um, I, we just signed this super interesting client. You know,

it's, it was for this much, this is their use case. Let me know if you

wanna chat about it more. That's it.

Like, just a quick drop.

[00:23:00] Or if you

know, you know, hey, you know, hey Matt, we just, we released this feature

that you were super interested in, like, or this was really right up your alley. Like, I can give you a demo

if you want. So it's just a couple lines little warm touch. They're

not gonna take you up on it most of the time, but that way you're staying on

top of their mind, right?

They're

not forgetting about you because analysts talk to

hundreds of vendors

And the need to have

a reason to remember you, and it's going to honestly be the, like the personal relationship, not the like, here's a

big news. A newsletter for analysts is great when you get bigger and you've got, and you're going large.

But when we're just trying to like really bond with one or two analysts, it's just the little

touches. And it

should be from the founder

ideally, right? The founder needs to to be. building that up.

Matt Amundson: Got it. Got it. Love.

Craig Rosenberg: Yeah. I, I, uh, a couple thoughts on this and then, uh, well, so one is, um, what I noticed when I was in the be belly of the Beast, so just for the show, I was at Gartner for almost three years, maybe two and a half or something. And um, so one is they're [00:24:00] normal people. That's very important for everyone to know, like

they're typical. They really like tiramisu, um, and they don't like Ethiopian food. I'll discuss that, uh, team building party later. Um,

but, um, yeah, so well they, you know, some of the, in, in our group at the time, a couple of them were germaphobes. It's not a good place for germaphobe.

Um, so, but one is. It feels, I, I, you know, I tell people look like you're gonna feel like it's didn't work for a while. You really are. Because, um, well one, they, they never, they don't really tip their hats. Like they don't, or, you know, they tip their cards like they are, you know, they're gonna to hear what you have to say. Um, even if, and by the way, even on some where they, it feels like they didn't like it, like I would've got, I could get off a briefing and I'd just be like, dude, like you didn't like that.

He's like, whatcha talking about? I just, I'm, [00:25:00] I'm just taking it in. Uh, what I noticed is, um, like months later, right months later, you started to see. Not all because they get, we get so many briefings. You started to see like the stories manifest itself into their writing or what they're talking

or how they're talking about things. Or you're in a big meeting and someone to say, oh my God, wait, I gotta go look this up. I just did a briefing with someone who solved for this. Those things are how this works. But you have to go, you just gotta do it and you gotta stick with it. Because if it's an interesting story, which you shouldn't start a company, if you don't have one, um, it will catch like, so it's really interesting.

Um. Obviously, as you guys know, you can't name names when you're in the, you know, the, but like, he, he was really, you know, a lot of the guys get really good, um, as I'm sure Rachel could tell you, at just creating this [00:26:00] big massive deck and then they'll cut up the deck when they're doing different briefings or you know, presentations.

A lot of 'em are like aiming to do as many presentations as they can. It's kind of a mark of like being able to travel to Singapore and do your thing and like I. I started to watch him. He was really good and I loved his stuff and he, he, we started, he, so I could see him adding stories from briefings over the year so that, you know, I was thinking, gosh, you know, that vendor briefed him probably in January and next January it's in the deck.

And

if you're in the deck you're getting a big mention.

And the other thing is if you sell enterprise software, like. Just to be clear, they still buy Gartner. They still listen to Gartner.

They still have really good relationships with those analysts. It's funny how many people try to push back on me.

That's 'cause nobody's been inside and listened to the calls that these guys take,

right? From like CIOs of Fortune five companies wanting to know what to buy for the year. Um, so I I I [00:27:00] love what you just said there. I think, um, what I saw, like on the. Briefing side was, um, you, you also, and this I heard from a, um, another consultant.

It's like you wanna leave them a deck that they can go back and reference off the briefing. Um, I needed that a lot. That was like my gold mine of information. Um. You know, whether we are doing a writing, writing or something later. And then the thing you said is they do want to know their technology wonks.

They don't love Dell. I mean like they, you know, they work with Dell and Dell pays a lot and they've been doing it for years and they have deep relationships with execs there. But they do want to be. The ones to know about what's about to disrupt

that is like, it's crazy to think otherwise, just it's the reactions you get and the time that it takes for things to, to come around. So anyway, those were my thoughts. But from your perspective, so like in the seed [00:28:00] company you just launched into the major firms, like when do, when do you set expectations for like what should they expect to happen running this playbook?

Rachel Dines: I mean,

this is a long game and like what you just said, everything you just said, I completely agree with it. To really get meaningful, like I would say it takes maybe two years of doing this consistently,

at least. To get any kind of like tangible

output. And I'm, a lot of people are like, oh

my God, are you serious?

We have to do this for two years. But the thing is, in the end, it's not a huge lift, right? Once you Get up and going and you figure out, 'cause I'm not saying go

do this with 10 analysts. If you're a seed stage company, find two analysts

who you think you can really connect with

and build a relationship over a couple of years. And then you will start to see,

you'll

start to see the, the outcome. And that might be, it'll probably start as. Inbound people coming to you and

say like, oh, I heard about you from Forrester. I heard about you from Gardner.

And

eventually

it may lead to [00:29:00] you being included in an evaluation,

uh, or, you know, a ranking.

Which to Craig's point, people still really, really look

at this and

not just the enterprise. I mean, at my last company at Chronosphere, like, yes, we sold to the enterprise, but we, we sold a lot to like,

we called them large born in the clouds, right? Like really large scale web scale, cloud scale companies.

And they cared so deeply about Gartner. And it took us years of hard work to get into the Gartner Magic Quadrant. When we did, we were a leader. Um, but it was years and years of work, uh, with almost no return. And a lot of people looking at me saying like, you crazy. What are you doing? It was like this, this will work.

Just patience, patience.

Craig Rosenberg: I

Matt Amundson: don't have enough people in my life saying, you crazy.

Sam Guertin: You

crazy.

Rachel Dines: But

Matt Amundson: I need that.

Craig Rosenberg: acting

Rachel Dines: enough apparently.

Matt Amundson: Uh, I mean, Craig can attest that I do all the time, but

Craig Rosenberg: Yeah. Well,

you can't. [00:30:00] Yeah,

he, he has road. He has road rage. That's

one

thing. Rachel, just to let

you insight. Yeah. I'll be talking on the phone with him. We'll be

like, hang on. And then just start cursing out someone who just did some kind of driving move. I'm not

Rachel Dines: Are you sure you're

not from Massachusetts?

Matt Amundson: mean, it's in my soul. It's Okay. Yeah,

Rachel Dines: I feel it. I felt a kindred, uh, moment with you. Yeah, that's,

I think you secretly have some Massachusetts roots.

Craig Rosenberg: Yeah. And then number two, he coaches, uh, a 14 new football team. And, uh, trying to keep those guys in line requires occasionally, you know, blowing his lid.

And so it's really intriguing to watch, uh,

Matt Amundson: I, I got so activated last night, Craig, at one point I was, I was, I was quite dizzy. I'm like, I'm not as young as I used to be.

Craig Rosenberg: Wow. Jesus, man. I, I did not, I did not know that one. Um, [00:31:00] so I, well, first of all, anything else on your list or you want to dig, keep digging on this 'cause I have a co I have a couple more, uh, things to dig in on there. I want to get, uh, you

and Matt's Um, I have more things to talk on the list, but I also wanna

Rachel Dines: give, if you'd rather dig, like if you think the listeners are interested in going real deep and real nerdy on analysts, I can also nerd out forever on

Matt Amundson: keep

pulling the

sweater.

Craig Rosenberg: I, I, well, let's just do one other thing, which is a more tactical set of recommendations for you. So we talked about it from an early stage perspective, but let's, let's talk about like, are there things that you do to be number one in the magic quadrant? And then like, what do you do when you're, you know, uh. You know, a late stage company or you know, public or big, like, is there any other things that we should be thinking about in working with the analysts? In, in, in that regard?

Rachel Dines: Yeah,

I mean, look, if there was a

secret, magic way to just immediately be number one in the magic quadrant, I would [00:32:00] be out there selling that right now. but there's not, right?

'cause there's just so much out of your control. But I think in all

of the evaluations,

it really, it comes down to the criteria. And looking at every single and like, I don't know if, for those of you who haven't taken the time to dig into like a, a wave or a magic quadrant, it's all like, at least in the waves, these are published.

It is long list of criteria. And the criteria are how they place everybody. And so if you're looking to, first of all, if you're not in an evaluation and you wanna understand where you think you might be. Download the criteria and from with Forrester you could, it's just in the Wave document itself. With Garner, it's the critical capabilities, which is this, it's a companion document. Um, download them and just work with the PMs on your team to do a really, and actually ses, ses, I feel like are the best at this 'cause they can be so cynical. Love ses.

Don't get me wrong, shout out to all the SEs in my life who, who I care about deeply, but They can be very cynical about your own product and they can be kind of very clear-eyed.

So go through [00:33:00] the criteria and try and do an honest assessment of where you're at,

um, where you're

weak. Figure out how you can

tell a story or maybe even you work with the development team, right? I mean, if it's something that's low hanging fruit, most people don't change their roadmaps because of Gartner Forester, but like if there's something very easy and straightforward, and the other thing you can do is try and change the criteria, try and influence the criteria.

They change it a little bit every year. And So I think it just comes down to understanding how are they.

Putting people where they put

them and where, you know,

where do you wanna try and move the needle on that?

Um, if

you're very lucky, you get to get in on the

ground floor of a new evaluation and they're coming up with the criteria for the first time, and you get to really shape the criteria from the start.

I got a chance to do that. Once, I'm not going to name a name on that, but it, we, it helped tremendously, let's just say it

was a very first

time that evaluation had come out and

we were very hands-on with the analysts [00:34:00] helping shape the, the criteria, and it was in our favor.

Matt Amundson: Very cool. Very cool.

Craig Rosenberg: Love it. Um, all right, go keep going on your list.

Matt Amundson: Yeah. Number two.

Rachel Dines: Number

two. Uh, okay. I put a bunch of things in here. Um, I guess the other thing,

oh gosh,

I keep seeing this and I'm curious if you all are seeing this

too. 'cause you also talk to a lot of startups. A

lot of startups I'm talking to lately. Have like

way too many use cases and way too many like target segments, and they

think they can attack all of them all at the same time

with a team of like 10 people.

And no Matter how many times

I want to grab 'em and shake 'em and be like, pick One.

pick one. It doesn't have to be the right one. You can change later. If

it's

wrong, just pick one. This is making me crazy

right now, and I don't, I feel like it's worse than it used to be.

are

you seeing, are You seeing? this too?

Matt Amundson: I think it's worse than ever. I mean, this is a classic problem. Yeah. Honestly, yes. I think pro, I think probably because of the AI [00:35:00] component and like I think it's a little bit. Um, the sort of the think the, the product leaders and the CEOs of these companies are kinda like, well, anyone can use the bot. It is really, really hard as an advisor for years and years and years. The biggest thing that I always, you know, one of the biggest piece of feedback that I was giving people, because I did a lot of advisory for MarTech and sales Tech was your product is not for marketing and sales. Sorry. It just isn't like when you're like, Hey, this is for both.

It's for neither. Like you cannot do that. And I think, I think to your point, like that's only been exasperated by, you know, newer companies coming to market with AI tools that are for rev ops. BDR teams, sales teams, marketing teams, uh, sales ops, marketing ops, customer marketing. You're just like, okay, okay.

Back it up, back it up, back it up. Let's find a core audience and let's go. Let's go get some product market fit before we start thinking [00:36:00] about who else we want to expand out to. 'cause I think one of the things that people lose sight of is it's really. Expensive to run a Go-To-Market strategy to multiple ICPs, or at the very least, even just multiple personas within a single ICP.

And it's also, you just don't have the resources to do it, right? Like you're gonna find yourself in situations where it's like, where's the content for. A rev ops person at a small stage company that is, you know, in the FinTech space and you're like, dude, I, I don't have it. I don't have the bandwidth to build for each one of these categories, each one of these personas and each one of these, you know, uh, company size segments.

So that's, I think that's a huge challenge. I always try to get people early on, let's just pick a lane and let's go win that. And that lane could be as narrow as, and I know we've talked about in Massachusetts quite a bit, but like this came up on a pod before. It's like, hey, like let's sell to every rev ops leader in Boston at a small company, right?

Like, go narrow, go win [00:37:00] that space. I know it's, uh, it's not gonna look great on a board deck, but like, if you want to go get your first 100 customers, you're much better off focusing down to like a very, very narrow ICP.

Rachel Dines: Yes, I. Cannot agree

more with you. And I think it is interesting you brought up AI too, that that is one of the drivers behind this. I mean, so I mean, so Craig, do you not you're not seeing the same challenge? No, I am. I was, I just was interested in, it's worse than it's ever been. And then Matt's, I think Bill, Matt brought up a good point, which is, you know, with ai, the flexibility is a trap

Craig Rosenberg: because you'll, you'll, be able to handle a lot of things. Uh, so the, the way I think about it is, at the end of the day, how old's Salesforce, like 30 years old, 20 years old, something 20,

let's call.

Rachel Dines: 20,

Craig Rosenberg: But the unit of one there is still the CRM, the SFA.

And like you, you need this thing that you all, you're always good at selling. And to [00:38:00] whom? And to, and, and, and, and you know, that rhythm you build around this like single unit of one and then you build around it, uh, later.

But like it took a long time, you know, for, for this to evolve. Now it's obviously evolved, it's enterprise software, but like. Even now, if you went in, if nobody goes in like a salesperson, who, that's our, like my mark of like, you know how we win it is like, oh, I wanna sell you all this stuff. And then at the end of the day, they're arguing all these, well, let's just do the SFA.

That's what you want actually, which is like this thing that is like your core unit of one that you sell and a core use case. To a certain person at a certain type of company and you get really good at it and you build off it. If you're all over the place, it's just impossible. And you know, I look at all these folks, it's like that have built great companies and it was. [00:39:00] Always, there's this unit of one. It's like Oracle is relational databases and still it, you know, like, and it's like that was the thing that sort of, that was that anchor piece that everything around the company revolved like ServiceNow. I remember working with them, it was like 15 years in and they're like, Hey, we could sell this to hr.

Okay, great. By the way, that took them years. To do too. And thank God they didn't do it until it was like 15 years in and they had just nailed the help desk. Right. And it's

like, um, that's the thing is you just gotta nail this thing. And then

Matt Amundson: Mm-hmm.

Craig Rosenberg: I think that's really important, which is you can switch it, you can, like I

just, one of our startups in the portfolio, they moved to a different use case.

It was a good one because they were doing fine. But the, the, uh. The time it took to onboard customers, uh, was unwieldy.

And so they, they moved to another, that's a good business decision. And they moved to another

one, [00:40:00] which is sort of faster, a little lightweight, maybe a smaller a CV, but like now you could build a company around that.

And then, you know, and so I, I agree. I was initially reacting Rachel to like, it's worse now. 'cause I, I did feel like. Um, years ago at Topo when we were doing an account based talking to people about being a, and just this conversation around the ICP seemed to be like

radical.

Matt Amundson: Mm-hmm.

Craig Rosenberg: and it's still radical.

Matt Amundson: It

Rachel Dines: Well, I, I still see, well, it's radical in that people are embracing it, but then they're

like,

I have 10 ICPs, and

I'm like, no. It's like, that's

not, it's, I mean, and look, focus is always, I think the greatest Achilles heel focus

in the Go-To-Market side especially is is always the greatest

Achilles heel of so many startups Right now. It feels so much worse to me than it ever felt before. And maybe it's because I'm talking to more companies and like I have the, the benefit of like, I'm not just in one company at

a time. I'm in multiple, but I think it's [00:41:00] because,

to your point,

Matt, actually this just occurred to me

because

of AI companies are actually getting to customer facing product much faster than they ever were before. Like it used to take a couple of years of development. Now it's like, you know, they're vibe coding their way into a product in a couple of months and they've not had Enough time to really bake in the Go-To-Market

strategy. Like it's, it's wild how fast

you can get to market now, like with, with AI tools.

So I, I think that might be part of it.

And also

like, yeah, because the, the flexibility is a trap,

right?

It's like, well, because we can customize it with ai, it can be for this person and this person in this segment and that segment and, and like, yeah, no,

Craig Rosenberg: Yeah, I

do think,

the other thing a really quick Matt, and then go is the, the, there is a really positive development on the technology side for ICP development,

Matt Amundson: yeah. you can, uh, use data. First party, third party [00:42:00] to make good decisions on the ICP better than you ever had before. You can translate it off paper. Like that was the thing is the people that did do the ICP, it was a piece of paper and

Craig Rosenberg: like, and now you can create the targeted. Count you, you, you know, a, you could use real data to figure out the ICP. You can use, uh, technology to actually take the ICP and actually translate that into a set of accounts and you can actually. Take your target buyer and apply them to the accounts in a way that's a lot easier than it's it's ever been before. So like that, you know, as we talk about this, there's a, there's a real advance in the market here that will allow you to do what, you know, what you guys are talking about in a way you've frankly never had been able to before.

But sorry Matt, I didn't mean to interrupt you.

Actually, I'm not, I didn't Please cut the, sorry, Sam, but

I didn't, but I didn't, mean to interrupt you.

Sam Guertin: No apologies are going into this episode.

Craig Rosenberg: Thank [00:43:00] you know, if we're gonna bleep something, just bleep the sorrys.

Yeah. We're we're fricking mass assholes at heart.

Matt Amundson: That's right. That's right. We're

leaning in. I, I, think, uh, I, I, you know, to Rachel's point, it's like the idea that you can go from literal idea to fully baked product in a matter of weeks now, I think is, um, it's, it's disrupting the sort of. Typical early stage business trajectory, which would also include, you know, building a Go-To-Market plan, right?

And so people are just kind of coming to market with these products that are. Quite frankly, very badass, right? Like, I think in the, in the, uh, you know, in the not too distant past, you know, you'd come to market with like this alpha product and you know, you'd need to find some friendlies who are willing to become your customers and give you product feedback and whatnot.

But like. You're seeing things that are like, wow, how long have you guys been in business? They're like, [00:44:00] man, five weeks. Uh, that are actually killer applications. Uh, you know, we just hosted at our company, we hosted like an internal sales AI hackathon and some of the stuff that, uh, our sales team built was badass.

Uh, I mean, it was very specific to our own environment. Not something that could be productized, but something that we could build process around. So I think. Uh, the, the set of tools that are, are in place today, like with the cursors and the windsurf and the lovable, like, they enable people to take these ideas that they've always had swirling around in their head and bring them to reality so quickly.

But the unfortunate part is for a lot of them, they're not, you know, they've never been operators before, and so they're kind of like, all right, well, I built this. Who are you gonna sell it to? And how are you gonna sell it? No, I don't know. Everybody would want this.

Rachel Dines: It is for everyone.

Yeah, and I think, I think,

on a few episodes ago you were talking about like the age of the Go-To-Market hacker, which I

love so much, and that's awesome that you're doing sales hackathons. I actually used to

do marketing hackathons with my team at Cloud Health. This

was before ai, but [00:45:00] like basically I was like, look, whether you're writing code

or building a tool, like building a spreadsheet, that's a, like a sales enablement ROI tool, like we would spend a day. Hacking at something and it might be a new

landing page or, and giving that, like, that technic that, you know, that was really fun. Imagine now if we did that and we actually had AI tools, I could just, you know, bring up my V zero,

uh, and my cursor and like, just type in, I wanna build an ROI tool. Uh, it's incredible.

So like, that's the other thing right now that's really blowing my mind is

like

the blue sky. Think people that can really be big blue sky thinkers with ai. Are gonna win right

now in marketing. 'cause like AI is only as creative as you are.

Right. Ex. exactly.

So, um, it'll give you whatever you want,

but you need to know what to

ask it.

Um, And it, I'm just very excited about it for, you know, certain use cases like it. Does it write blog post? Well, no. Does it edit my blog

Craig Rosenberg: my blog

goes well.

Matt Amundson: yes.

[00:46:00] Exactly.

Craig Rosenberg: I, uh, I, I totally agree. All right. So, um, any, any more on your list? We have.

Matt Amundson: We've had two great ones, right?

Yeah. They're all

Rachel Dines: I think Those were my good ones. I mean,

my other ones

Matt Amundson: Give us your bad ones. Give

us the my bad ones. Okay. Okay.

Rachel Dines: Um, well, okay, I have bad ones then. I've got like my got like my other red story. tell you.

Um,

Craig Rosenberg: Matt. Alright, go. Bad ones first.

Matt Amundson: Well, no. Do you want stories? You got very excited around stories.

Rachel Dines: I mean, I am well, fun story about how I give I get terrible advice sometimes, Oh, is a self-deprecating

Matt Amundson: want that.

Craig Rosenberg: well that's good. Matt needs to hear this.

Okay. Have you ever given someone really bad advice?

Matt Amundson: multiple times a day. I have two Okay.

Rachel Dines: Yeah,

Craig Rosenberg: Yeah, I mean I've

Rachel Dines: kid and

he, he never

Matt Amundson: See, I, I give twice the bad advice. There you go.

Craig Rosenberg: Two x, two x. Yeah.

Why Your First Marketing Hire Should be a Product Marketer
---

Rachel Dines: Um, well, uh, well, okay, so my, my

my other, my not so good hot

take was people are hiring heads of marketing way [00:47:00] too early. And your

first marketer should be a product marketer, also, a

self-serving con uh, idea,

Craig Rosenberg: Wait, that's not a bad take. Let's talk about that.

Matt, do you agree?

Matt Amundson: So I have an evolving take here. Which is for years and years and years. I said, actually the first marketing hire you should hire is demand gen. That was my take from probably 2013 to 2023, like solid 10 years. I was like, you have to, because my, my belief always was like, Hey, look. CEO should be able to articulate what the primary value props are, and you should as like.

Uh, a decent, well-rounded marketer with a strong background in demand gen, be able to take that and turn it into strong marketing campaigns. What I am telling early stage CEOs now is. You should hire a product marketer first because if you can't nail your [00:48:00] messaging, you cannot fuel your demand gen with something that's actually gonna turn into repeatable pipeline.

You just won't. You just won't. And, um. Yes, A CEO can do that, but like nowadays, like the, you know, maybe always they, they, they don't really have the bandwidth for it. And I think in a lot of cases, like what I was seeing in the earlier 2000 tens was more CEOs were, were sort of, uh, came from the Go-To-Market or came from the finance side.

Now we see many more CEOs that are, are former engineers, almost sort of across the board. Right. And so, you know, they generally, they have less Go-To-Market knowledge. And so utilizing them as a resource, as part of your go-to-market strategy is, is trickier. It's not impossible, it's just trickier. Uh, and so having somebody who can come in and formulate the message and as well as the company narrative, which is a thing that I think a lot of people don't.

Necessarily think of those as being, uh, um, sort of an A and B. They think of [00:49:00] them as being one thing, but you have to have a company narrative. Why did we start? Who are we serving? What is our long-term mission versus just what is our product and what does it do? Uh, those are two separate things that. One is more of like, Hey, how are we going to go tell our story whether we're speaking to an analyst, as we talked about earlier, how are we gonna tell our story on our website?

And versus like, what's gonna go out in programs and actually hook people and get them excited about what we do, because they probably won't care that you started in 2023 or something like that.

Rachel Dines: Yeah. Can I add one onto that

Matt Amundson: yeah, please do.

Rachel Dines: not to, because I think I agree narrative messaging, but then one more positioning. Where do you sit in the

market? How do you.

fit with other players in the market? What Who are you? Who are

you not? That's the other big one. I've been working with a lot of companies on

lately. Sorry,

just to interrupt. Just

Matt Amundson: No, I, I think I, I think that that is a really important point because I see fewer and fewer companies actually doing that. It's weird. They sort of rely on the analyst, uh, world to say, this is how [00:50:00] everything gets positioned together. But I think one of the things like, that's like a, a little bit of a sneaky trick here is like, let's say you're in the AI space.

And maybe you don't compete with Cursor or windsurf or lovable, but you're a complimentary product to them putting out content that shows how you're a complimentary product to them. Even if you're just creating visuals for like how a stack would come together, how a workflow would come together automatically starts to, uh, put you in the market as like, oh yeah.

If you're a cursor user, if you're a windsurf user, if you're a lovable user, you're. Inevitably also gonna be a whatchamacallit AI user, right? Like that is a really strong play that almost no one is doing. And they're all just kind of like, well, I hope someone's gonna put this content together so that we can reshare it and put it on our website or whatever.

Just go out and build it yourself.

Rachel Dines: Yeah. Yeah, just do it. And like the, if the analysts come along and have something similar, amazing.

Matt Amundson: Yeah. you can't they're, yeah.

Craig Rosenberg: Okay. I like that. That was a good one. I think, um, [00:51:00] I will just say that, you know, we had, um. I, I think that's shared with a lot of, whoa, is someone getting electrocuted right now? Is that you, Sam? He's constantly

getting electrocuted. It's a problem. The, um, but the CMOs that, you know, I've worked with besides Matt, Matt's worked with me.

I've had six or seven here at the firm.

They always say, well, these guys need product marketing first. But I, I don't know that that's the instinct of the company or the board. don't know

Rachel Dines: Yeah, It

It seems to be less common than I would, Ima than I would think that I'm, I, it's, I'm always surprised that product marketing's not the first in the door for all the reasons Matt just said, right? Because yes, the CEO can tell the story, but that's not the best use of their time. A and b, a really good product marketer can distill that story and make it.

Scalable for everyone in the organization. 'cause like I've come into a lot of companies where I was the first product marketer in.

house and the story could only be [00:52:00] told by the CEO and the CEO O told it

amazingly and no one else could tell it. And so my job would've been like a great product marketer will take

the CEO's vision and store or the CT o the founder's vision and story

and package it into something for the

market and package it

into something the whole company can use.

And the whole company can speak in the same voice together

Craig Rosenberg: together.

Rachel Dines: story.

So.

Craig Rosenberg: Okay. I like that.

Some not so great career advice
---

Craig Rosenberg: Now let's get the, we got, uh, story number two.

Rachel Dines: Okay, I will

just to throw myself completely under the bus

and make

me completely uncredible for the rest

of everything else I've just said.

Um,

Matt Amundson: people don't stay

this long into the podcast. You're

Rachel Dines: Okay, good. good. Then no one's gonna hear this, this story. So, right outta

college, um, I graduated,

uh, basically

right into like the Lehman Brothers crash and complete, you know, garbage of, of, uh, a market.

A bunch of my friends, I was very lucky and I got a job right

outta school, but a lot of my friends were really struggling in the job market.

My best [00:53:00] friend, uh, was, was struggling a little bit. She finally, she, it came down to two companies. She had two pretty good offers on the table. One was from like a really big, uh, like, and she wanted to go into market

MarTech, like at the time, I don't remember whatever we called it.

And one was, one offer was from like double click

or like some really big, you know, advertising company at the time.

And the

other was from this like seven person startup that made something that didn't sound like it could ever have a real market. And it sounded really dumb. And so I told her like.

Do not take that job

at that seven person startup.

Like

that's never not going anywhere.

You're, you'd be idiot not to. You know, you gotta take the job at double click. Luckily She didn't listen to me because that

seven person startup was HubSpot. Um, and. We're still friends. Luckily, she,

luckily she didn't listen to me. Um, and, uh, I was like, nobody wants mar no one needs a software for marketing operations.

This is the dumbest

Craig Rosenberg: Dumb thing I've ever heard.

Rachel Dines: Um, so clearly I'm[00:54:00]

Craig Rosenberg: You know what? I, I actually can, can vouch for that. That story is uh, uh. I get it because you know what? I don't, people ask me all the time, and I do not give them a definitive, I queue them up with my take on all their options and hope that I can help them. That's my new thing. Like people are trying to cheat because one, many of them don't listen anyway.

So like you just spent all this time giving this advice and then they went the other way.

Uh, right. And then, um, um. I would say, now I'm right, not in start, startups are too hard.

You gotta like, you just gotta let people go. There's vibe, that's vibe not recruiting, you know? Uh, but you know, you're, you're basically doing a vibe higher.

You're like, you're trying to, you're choosing based on a lot of other like, really personal factors there. But I mean, later stage, I [00:55:00] typically can tell people. You know, whether I could tell whether someone's gonna hate it or not. I still, and so in, in, you know, I would be right if I would give people that take, but since, uh, 70% of the time I've given people advice and they went the other way, I've just given up and just set myself up for success by providing them with my take on all sides and doing positives and negatives for each one.

Rachel Dines: That's smart.

I was not that nuanced at 23 years old. Um,

Craig Rosenberg: Yeah. No, you did your thing.

I love it. That's a great story. I, yeah, I remember talking to Chris Degnan about Snowflake and we were meeting in Palo Alto and he's like, yeah, dude, it's weird. There's like 12 engineers in this office and like I would just be selling the stuff myself. I was already in the rules, so I didn't say, okay, well like, you know, do you feel strong about what you could sell and whatever.

And he ended up choosing that. And now, you know, he's building his estate in Lake Tahoe, um, as he was the first guy in there, you know, from a [00:56:00] Go-To-Market perspective, it was pretty amazing. Thank

God, at that time I'd already figured out they'll give people advice on startups. Um,

Matt Amundson: those, those snowflakes, man, they just, they did so well. You know, I was, uh, I was at a dinner not long ago with Denise Pearson and like the, just the Denise Aura is like, she just, it was like at night she walked in, they might as well just turned the lights off. She was glowing. It's just like, God, what that has done for those people, just, oh my God, like, just come with lighting.

I mean, she, you know what? I,

Rachel Dines: Yeah,

I'm in all those That's what we feel about the HubSpot people.

Like that's HubSpot's our big Boston hit.

Um, obviously I'm so happy for my friend and she went on to do another very couple more successful startups too,

and, good for her. doesn't listen to my advice. Pulled more

Craig Rosenberg: Yes.

That, that's, that's the moral of this, uh, podcast. Whatever you heard today, don't follow

Matt Amundson: Don't follow it. Yeah.

Craig Rosenberg: do well, um, that was, see Rachel, you did great.

Matt Amundson: Fantastic. What [00:57:00] a great

Craig Rosenberg: a

great show. Yeah. You had, that was fun. And you had really great takes and you were funny. You told

Matt Amundson: You're in a forest.

Rachel Dines: I am in a forest. My husband

Craig Rosenberg: Wandering Wandering around around behind me great. them to get the hell outta

here.

Uh, no, that's, that's even better. I, we, we, we, uh, we appreciate you being in the forest. I love this kind of a, uh, you know, uh, west coast, east coast vibe. I've

got Foster City behind me and Matt is likely Matt lives right over there,

so

Matt Amundson: Yeah, just on the, yeah.

Craig Rosenberg: Yeah. He's

Matt Amundson: Yeah. You can't tell 'cause I got the beige background.

Craig Rosenberg: Yeah, it looks like he's in, you know, prison with El Chapo,

Matt Amundson: yeah. The waters of Foster City look very tropical today. from I, I was about

Craig Rosenberg: was about to say You look

like

you're in like the,

Rachel Dines: or something. Why is it so tropical?

Craig Rosenberg: well, foster City's kind of the Caribbean of the Bay Area,

Matt Amundson: It really is. A lot of people have said If

Craig Rosenberg: you want to grade a, if you want to grab a five guys and pick up your CVS prescription on your [00:58:00] way to the water, it's a really good place. Um, actually fi Yeah, it looks beautiful today. It's amazing when it's like this because Matt and I used to marvel that there's nobody on the water.

I mean, like literally nobody out there. And it's beautiful today and I mean, hey, you know, are we gonna do?

Matt Amundson: They do dye the water though, so I think they maybe have freshly dyed it. So you might wanna stay outta there for the

Rachel Dines: Do they really

Craig Rosenberg: Do they really die? Yeah,

Matt Amundson: to.

Craig Rosenberg: they diet. It's a weird, it's like this weird slime when you go in. It feels really weird. Um,

but, uh, yeah, uh, it's, uh,

Matt Amundson: They didn't die it during the pandemic and it got, it's just brown. It's just,

Craig Rosenberg: it's a fun fact about Foster City. You can't see it, but the Bay is out there, which is, you know, like it's so brown compared to Foster

City's lagoon. Yeah. Yeah. Yeah.

Matt Amundson: [00:59:00] yeah,

Craig Rosenberg: Is it, is it called the Lagoon in Fo?

Matt Amundson: It

Craig Rosenberg: right, but it's a fake Lagoon.

Matt Amundson: It is foe. Yeah. I mean, yeah,

exactly. Foster City's man. The whole, the whole of, it's just manmade. It used to just be the Bay. So

Rachel Dines: Oh Yeah. I haven't been there in a long time.

We, Well come on back. Come on

Matt Amundson: back. Alright. Alright. I got you. welcome me back. We've got a, we got a spot for you. Okay, great. Great show. Thank you so much. I'm so glad this worked out

Craig Rosenberg: and, uh, have a great, thank

Rachel Dines: me. This was

really

fun.

Craig Rosenberg: Yeah. We'll do

it again. We'll do it

again. Okay.

Um, we're, we're like analysts.

Just keep sending us your ideas and stories and

Rachel Dines: Oh, yeah. I'll keep pitching you. Sounds good.

Craig Rosenberg: all. [01:00:00]