The Transaction

All right, I've hit record, everyone.

Thank you.

Yeah, I see that it's recorded.

Yeah, no, it's part of my skill set for writing these podcasts.

You know, I hit record, and then I hit leave session at the end.

Oh, I have the word to describe Carilu, or the phrase.

Oh, phrase.

We'll introduce you.

We like to start, we like to tempt people by having a conversation that starts, okay, because I initially talked about B2B Famous this morning.

You were there?

I was.

What about B2B Fabulous?

Should people say that?

Like, no?

Over the top?

Seems like maybe I should have some, like, feathers in my hair.

Yeah, you're at least one feather short.

But like, we were talking about, so as we lead into this Carilu, there's this interesting thing called B2B Famous.

You know, we've been around for a while and there's these people where you see them, right?

Because of content, because of speaking, just people mention you all the time because we work with Maria, so we hear about you literally at every conversation.

By the way, fun fact, Maria Pergolino talks about Carilu all the time.

But we know about you, we feel like we know a ton about you, and then years later, we meet you, years later.

It's one, like it's so like, you know, it's like this, in B2B, we don't get it as much.

You know, obviously, in the world of consumer and influencers and all that stuff, we get that all the time.

It's like, you know, I don't know George Clooney, but I know a lot about George Clooney.

But like in B2B, we don't get that all the time.

Our guest today, Carilu, falls into that category.

I think we all sort of started to learn a lot about you during when you were leading the marketing at Atlassian to a wildly successful IPO.

And then from their content and being out there perspective, that's where your B2B fame just continued to grow.

Now you're like, I can't even list the amount of companies you advise, you know, as an advisor.

And it's pretty amazing that you're sharing all your knowledge, but you share it with your clients and customers, and then you share it with the world because like following you on LinkedIn is a goldmine.

And so it's like, it's an honor, it's awesome to have.

She left.

And she's out.

She was sick of your intro, dude.

It's too much.

Great intro.

Really?

I felt that though.

It was coming from the heart.

It's coming from somewhere.

From ABM to PLG, from Meddic to Meddpicc, the world of business is constantly evolving.

We'll cover the who, what, where, when, why, and most importantly, how you get The Transaction.

I'm Matt Amundson and he's Craig Rosenberg.

Let's get started.

Well, it's funny because you can make fun of me for doing that over the top.

I mean, I think she is over the top intro and then she just left the call and just going, this is outrageous.

I think you lost her at B2B Fabulous.

Why?

Is that that bad?

It's interesting.

Well, you guys next did anyway, so it's okay.

Oh, there she is.

Oh, hello.

Sorry, it was frozen.

It just froze when you were giving me the nicest intro.

I know.

I'm probably going to read because we were talking on the backs because Matt accused me of using B2B Fabulous and you running off the show because I said that.

So, Carilu, thank you so much for coming on the show today.

Thanks for having me.

That's so many nice compliments.

You know, I feel like I'm still just a voracious learner and a mid-level manager trying to learn as much as I can from all these fantastic people around me.

So, you guys included it and it's good to be here.

Thank you.

We don't believe you on that last one, but thank you.

Well, he talks through it all.

Well, Maria talks about you guys all the time, too.

And Maria, Maria Pergolino is the CMO of Active Campaign and a number of other companies.

And I pretty much hunted her down and made her become my best friend because I thought she was one of the smartest CMOs and really deep in the details.

And then so much more comes with it with her interest in art and her her creativity and all sorts of things.

But yes, I'm always trying to hunt down smart and interesting people.

And you guys are on the list.

I've been excited to be involved with Scale Venture Partners and get to spend more time with both of you.

Thank you.

See, that was that.

Should we end the show?

No.

Yeah, I'm good.

All right.

Here.

So here's how we like to start the show.

We like to ask this question, you know, for, and I would just contextually, like, we just want people to rethink, you know, their approach, right?

So we ask all our guests to start off the show.

Like, what's something, whether it's a approach, a methodology, best practice or whatever, that the market thinks they're doing right, but actually they're wrong and they should be rethinking it and what should they go do about it?

And that's how we start things.

So I'm gonna start there and give it to you and then we'll see where this goes.

I don't think your C-suite will survive hyper growth without a really good team of advisors around them.

And I think a lot of early stage companies get advisory from their venture capitalists or kind of a hodgepodge of their close friends, but those that have really surpassed normal growth rates and not turned over most of their executive team have a really skilled group of advisors supporting them on a lot of different fronts.

So I'd love to talk about advisors today.

So that is radical.

By the way, another note on a previous guest, Dennis Lyandres, when he was talking through the things he would recommend to people, one thing he said is, surround yourself with people smarter than you.

And he always had a set of advisors.

And thankfully, I was one of them.

I wasn't the smarter than him one.

I was the one that did some other things.

Okay, so tell us more what that means and what that looks like.

Because I think that is a radical answer to that question.

So let's dig into that.

Well, when you're an up and coming leader, you think about hiring people smarter than you as your leadership team under you, right?

If you're vice president, and you're going to hire some of the smartest senior directors you can to help you in an area you're not strong.

That's kind of taught in our normal curricula.

But generally, up and coming leaders don't have the money or access to get senior level advisors that the CEO or the board might be able to introduce.

And let's talk about a couple of different models, right?

Because you're right, I was at Atlassian from earlier stages through IPO and being public, heading marketing.

With a number of amazing people, I definitely can't take credit.

Everything about the people that works there and across the teams is fantastic.

Bootstrapped, took no investors, and they only took investors when they actually started to need networking connections to hire even greater people, partnerships, introductions.

They felt like they needed advice, and they took an investment from Excel.

And Excel was the only investor ahead of our IPO, and it wasn't even money we used.

It created some liquidity for long-standing employees.

And I also advised OnePassword, which is one of the leading security companies out of Toronto, so outside of Silicon Valley, good people outside the echo chamber.

And they were also bootstrapped and took money also from Excel just to get introductions to elite people and networks.

And that's actually how I met them and started advising them through my Excel connections.

So some people get it through their investors.

Some people have friends.

You know, we know if you like went to Stanford or HBR, you've got a really nice network and some great advisors you can call on.

Most of us didn't have all of the pieces that led to that possible outcome.

And again, it's like who you know.

Like if you live in the Bay Area, great.

Maybe there's, you know, the football coach down the street whose wife is some executive who can advise you.

But for a lot of entrepreneurs and top executives around the world, they need access to people who know patterns ahead of their scale of growth, who know people and agencies they can trust and introduce them to you and have social capital to encourage people to come work for companies that could otherwise be a risk.

And so this network effect is really accentuated if you can hire the right advisors or entice the right advisors to help you.

I love that.

Yeah.

I mean, yeah.

I've been on both sides of the fence, right?

So I've operated both as an operator who's had access to advisors.

I will say some situations were significantly better than others.

And I've also operated as an advisor.

And the only time I ever take on advisory, you know, when I'm not working directly for a venture firm, is if I actually think I can help them, right?

Because one of the things that can be really tricky when you're an operator and you're working, you know, maybe you're working with a fund or PE., sometimes you can get force fed advisors who aren't actually the right people for that stage of growth.

And that's one thing that can be a little bit challenging.

And then I think for a lot of people, they can lose a little bit of psychological safety as a result of being sort of, hey, I'm going to give you this advisor.

How do you think about the relationship for somebody who's maybe a VP or in the C-suite who's being introduced to an advisor, either from somebody who's made an investment in their business or their CEO who's saying, hey, I want to introduce you to this advisor who's going to help you out?

Trust is the biggest currency we have in business.

As a leader, when I was at Atlassian, we were doing something almost no one else were.

We were innovating product-led growth.

I couldn't find a lot of people that knew that.

I was young, I didn't have all the CMO friends I have now.

When I had run awareness advertising at Oracle, I had this massive budget.

I was spending $40 to $60 million.

I was invited to every Wall Street Journal, New York Times, Wired event, there was.

But when I was the head of marketing at Atlassian and we were small and a no-name dev tools company out of Australia, I wasn't getting invited to anything.

So my access to try to create connections myself was tenuous.

So I would go to all these CMO events, I would try to meet people, I tried to hustle, but I had a crazy day job.

I was flying back and forth to Australia, I had two little kids, my mom had just passed away, had an hour commute each way, didn't have a lot of time to build that network around me.

So I think anyone at Atlassian would have given me, I would have gotten something from, I would have really appreciated that, because when you're the top marketer, no one else at the company has more marketing experience than you do, and you can't talk to everyone on your team about your challenges, because some of your challenges are, should I fire this person?

Should I reorganize this?

Should I invest here and not there?

So it's very lonely.

But I get your point, like if someone is brought in to investigate your performance, there's definitely an aspect of anxiety and trust.

I mean, I think it depends on your relationship with the advisor and your strength in the role.

And if you're open, you know, one of the worst conversations I ever had was with the CMO and one of my friends who's a VC and was her president at the time.

It's like, oh, I need you to come talk to my marketer.

And I was like, great, I would be happy to.

And we sat down at breakfast and she was like, I've got it.

I don't need help.

Thank you.

Oh, okay.

I was like, sweet, like, let's have breakfast.

Like, tell me about your kids.

Like, great.

And she did not last long.

Like if you're not open, you know, she was like, so defensive that she wasn't open to saying, you know, hey, I'm thinking about this or that, you know, like if she'd come with like some thoughts, I wasn't actually in critique mode.

I really was there to help.

At the time, I wasn't an advisor and I didn't want the job above her.

I was doing it for a friend and would have, you know, gladly just collaborated.

Every advisor brings you something, you know, you can learn something from all of them.

I mean, there's some bad advisors out there too.

And, you know, CEOs get bad advice and hire the wrong people.

So you gotta take everything with a grain of salt.

I think for me and the advisors I'm choosing, you know, it's like becoming friends with some of the CMOs that I've chased to become friends with over the years.

It's about evaluating the actual experience they've had, the hands-on practical tips they give you now, how much they're listening to you versus telling.

Like one of the problems I had with advisors was everyone's got advice and they might not know your business.

Right.

Like the advantage of a full-time advisor is that the structure that I use is that I'm deep.

Like I'm in the annual financial plan and the conversion rates and the metrics dashboards.

I'm usually talking to the CRO and the CEO and the CMO in order to give the CMO really good contextual advice.

When I would meet with this or that advisor or even our board member at Atlassian, you get to talk to them once a quarter.

They'd have some broad thoughts but they wouldn't really understand all of the challenges and obstacles.

I think it's a challenge, but I think the more access you get to networks of good people who can introduce you to good people, you should take all those opportunities you can.

Nice.

Let me reframe my question because I think I led with something slightly negative.

Let me err on the positive side now.

The best relationships between executives and advisors look like what?

When I first started coaching, let's say coaching, I came because I was looking for a coach.

I tried all these coaches.

They were mostly like leadership coaches, but they had some business experience, but it wasn't as a CMO, it wasn't in a hypergrowth company, certainly wasn't with PLG, all sorts of things.

I was in this one coaching meeting where the coach was like, and how does that make you feel?

I was like, it makes me feel like I want to know how to do my job.

Like I want to ask them when you can tell me how to fix these big problems, and then I would feel confident.

I started by coaching CMOs, but I very quickly realized that a lot of CMOs problems aren't actually the CMOs.

It's the system problem of the company.

So I realized that in order to help the CMO, I needed to be talking to the CEO too.

One reason is marketing is where strategy hits the market first.

So if you're targeting the wrong audience, if your product's not differentiated, if you just don't have product market fit yet, you could blame your CMO for not getting enough leads.

But it's not actually their SEO optimization that's the problem here.

It's something that's much farther upstream.

And if your marketer is under the gun and behind on delivery, they often don't have the social capital to tell the CEO.

Not a marketing problem.

It's actually a product and a market problem.

Let me show you some information about people not buying what we want to sell.

So being able to speak truth to power as the advisor is very useful.

And that's useful for my marketing clients too, because they're a great marketer.

We have some other problems here.

Or another really common one that I know you two have been through is when a company is moving into a sales go-to-market model and hires too many salespeople too fast.

And it's ahead of demand for the company.

And suddenly, marketing is doing a bad job because there's not enough pipeline.

If you look at the backward performance metrics, your organic traffic might not have quadrupled the way you quadrupled your sales team.

And no matter how much money you put in to advertising, it never converts at the same high rates as organic.

So if you don't have word of mouth, if you don't have momentum and you over hire sales, if marketing looks like a problem, let's fire the marketer.

As an outside advisor who can see all the pieces and is in multiple different companies and has lived a lot of these scripts before, it's really helpful.

So to answer your question very specifically, I think an advisor who's tied into the CEO and some of the other executives to get context, who's working regularly with the person, I generally meet with marketers every two to three weeks, where both sides are open-minded, where the company is open to advice but takes it with a grain of salt, and that the advisor isn't just trying to teach their playbook, but is really open-minded to being a thought partner for what's happening now.

Yeah.

Because I do think the other problem is, or where I've gotten advisors that maybe weren't the best fit or heard other people complain is where they feel like someone's bringing a really dated playbook.

Someone told me once, like, I thought I was going to have to, like, meet every couple of weeks with this dinosaur who was going to waste my time.

You know, but you're great.

Wow.

By the way, I would note that Matt didn't ask a question.

He did a Mad Libs.

Yeah.

That was pretty cool, man.

I'm going to give you, I just wanted to do a shout out to you for doing a Mad Libs-type play there.

Well, you know, I'm evolving.

They should be shorter.

They should be three words.

Lemon, hopscotch, bower.

I actually, that last part, well, the dinosaur thing, being a dinosaur, I just want everyone to know that I continue to learn and evolve.

But the advisor that brings a narrow point of view, unless you're squarely in that point of view, that's fraught with peril, right?

And the game has changed a lot.

So like, I'm running into folks and they're like, well, you got to get MQLs and it's like, here's the serious decisions waterfall.

It's like, you know, 2008-esque type of advice that they're providing.

And to be able to listen and to learn yourself as an advisor, you know, it's funny, we just talked about Maria Pergolino, she kept going, well, this could be hard because I'm used to bigger companies.

And all she's done for, you know, so because we have an advisor, I built an advisory function here at Scale Venture Partners.

And so, you know, the one we were talking about before, Maria has, you know, I couldn't wait to have her, right?

She was the smartest people, hardest working people, I know.

And she was like worried because she had this sort of different perspective as she worked with folks that were in Series A.

And because as an advisor, she listened and really understood their business.

And as you said, also has, in many cases, her most successful work is CEO founder perspectives as part of that work.

That has made her an invaluable, probably surprising to herself.

The other part is, as an advisor, she's still learning herself.

So she's watching and learning from all the other Series A folks that she's working with and outside taking in all these new things that are happening so that she can be affected.

But the big one is CEO founder, CMO relationships, understanding the business, evolving your advice to their business.

I feel like a couple other things I've noticed now that we're doing advisory work, I'd love to get your thoughts on.

So one is there is the early marketer or marketer going into a new market, trying to do new things that needs to learn really specifically new tactics or motions, etc.

I thought that would be the predominant use case.

What I've found, which I think Carilu sort of alluded to before, the good CMOs at more mature companies that are doing really well, they are folks that I thought we wouldn't work with them as much, but that's not true.

They need the thought partner that they can have a third party set of eyes to run ideas by to get different perspectives.

If you ask Maria, some of the more mature CMO advisers, she's like, well, they just need to talk it out.

If I spent an hour and I agree, I might give some different thoughts on how you present it or talk about it.

But just per your point, having smart people around you and advisers, I think it's a way of life no matter where you are in the process or what you need to learn as either as a thought partner, either to get really specific or to just have someone to run your ideas by, I think is amazing.

Carilu, you've learned a lot because I've heard you talk about the new playbook stuff.

You bring that to the table.

If you think about it, you at Atlassian, at this really new point of view, you had to learn and you're now an expert on PLG hyper growth.

But you can talk about any part of and have advisor relationships on any type of go-to-market motion because you're always constantly learning too.

Sorry, I interrupted you.

I actually just wanted to talk.

That's it.

Now that I've talked, go ahead as you were.

Great job.

I was going to emphatically agree with you and compliment the Scale Venture Partners' advisors because you guys have built a really strong advisory bench within Scale Venture Partners for your portfolio with some phenomenal CMOs.

Your portfolio is lucky to get them.

Yeah.

I mean, I'll tell you, I was terrified not continuing another massive CMO role that I would become dated and irrelevant.

And part of what I love about advisory is the advisories made me way more experienced and way more relevant because it's accelerated learning.

I mean, I'm seeing it between six and 15 companies in a really deep way per year.

And with that much context, and I can see across portfolios what's happening in the market.

I won't say better than a VC because certainly VCs sit on so many, but at an operating level, right?

Sometimes we just share with the board highlights of what we want them to know, and we're struggling with a lot of the pieces.

I'm seeing behind the curtains into a whole bunch of different companies and how the S&B market is acting right now and how the enterprise market is acting and how PLG performance metrics are changing and how enterprise sales performance metrics are changing.

So yeah, I took a personality test once, and one of my factors is like voracious learner.

So like I said on the beginning, I don't feel famous at all.

I feel like I'm just trying so hard to learn as fast as possible and then share that information through my blog at carilu.com or at events, meeting with other executives.

I'm just always on the hunt to try to learn for people who have great experience.

And of course, right now, all of us to learn and enter these new networks around AI.

I mean, I think that there's been like in a really established social pecking order.

Like, can I call it in the SaaS cloud space?

You know, we know who's on the Cloud 100 year after year, and you know, some of the CMOs that have been in the top spots.

And now there's this whole AI space, and I've advised a couple of companies in it like Weights and Biases.

It's at this next desk of a new group of people.

And so really like learning from them and helping that crossover and helping all of us cross over, it is an exciting time.

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So finding an advisor, is that, I mean, how do you do that?

Like, so let's say someone goes to the show, they're like, you know what?

I totally agree with that.

So how do you find them?

Well, I definitely think a lot of people find them through their investors.

So I get introduced to a lot of companies through their investors.

And it's actually a good mechanism because the CEO really has to be involved.

Like, for a lot of people with sophisticated experience, if I had tried to hire them as the head of marketing at Atlassian when we were small, I couldn't afford them.

They wouldn't have given me the time of day.

Like, almost everyone you want to learn from is too busy to help you and makes too much money for you to hire.

And the very best CMOs are not writing content and speaking on podcasts.

You know, a lot of the people that I really admire, I get to, like, pick their brain once or twice a year.

And it's not even public, right?

Like, last year, I interviewed Rick Schultz, who's the CMO of Databricks and an old friend of mine from Oracle.

And I had, I co-hosted him on a session at Saster last year.

And I wanted to do research and be like, oh, what has Rick talked about?

And there were, like, no podcasts, no presentations.

Like, Rick Schultz, leading Databricks, has done amazing things.

And you, like, you can't learn him in the public way.

So if you get introduced to people through your VC and through your CEO, that's a major advantage.

Also because the company can pay for them partially with equity instead of cash, you know, when you really don't have that that much money.

So unfortunately, like, you know, one of the topics I had thought we might talk about is a quote, like, I think long-term success is a network game.

And finding your way into the right networks, an advisor is one way to find your way into the right networks.

Your investors is one way.

And so in some ways, you kind of have to follow some of your trust networks to get to these different advisors.

Which is tricky to say, like, how do you take the first step?

But through the smartest, most well-connected people you know.

That's how.

That's beautiful.

All right, so on the networks, there's some more idea though, right?

Like you're trying to surround yourself with people that you can learn from and add value to.

So no matter who you are and in what position, the networks you build is one of the most powerful things that you can do for your success.

Absolutely.

And it's hard to get to the right networks through groups because there's like vendors who offer a lot of things, right?

Like the vendors want to bring all SDR leaders or all sales leaders or all CEOs together, but they really have an agenda.

And then industry groups, for them to survive, they have to be much broader.

So maybe it's not people that are your company size or not in your industry.

What you really want is an advisor is someone who knows about your industry, knows about your sales and go-to-market model, has seen the next two or three stages of growth, right?

If you're 10 million, you want someone who's seen 10 to 100.

If you're at 100, you want someone who's seen 100 to 400.

If you're at 400, you want someone who's seen 400 to 2 billion.

You want someone who's in the next stage of growth.

You want someone who's in B2B, not B2C, right?

Those are very different models.

And then in your role, right?

You know, like for me to have a CRO of a B2B tech company as my advisor would be helpful, but it would be easier for me to have a marketing leader.

And so that really narrows the field pretty quickly.

So there's some groups that have done a better job than others, but I mean, I spent years hopping through different CMO groups looking for what I was looking for.

And in the end, some of the best connections are just ones that I've forged one-on-one through like, I want to call it sales outbounding, except it was like friend outbounding.

Like one of my best connections I made when I was 21 and I was a PR man, entry level PR manager, and I made the connection because I was at this little company that was the same size as this other little company called Salesforce.

And I called the PR person who was on the press release and was like, hey, I do PR too.

Want to meet for lunch?

No way.

I made friends with this woman named Jane Hines.

And if you're in the tech PR world, you know Jane Hines.

She was the head of on Salesforce comms forever until she became the head of Google Cloud comms.

Like she's just like the baller of comms.

And then she ended up having a friend group that she'd have drinks with, which we called the PR nerds.

And it was literally the head of comms for every major highest profile PR tech company around.

So it was like Slack, Disco, Atlassian, like everyone, I don't know, GitHub, like everyone who was amazing and a couple of the agencies.

And so my outbounding to make a friend, like looped me into this little network.

And then that network made me friends in other networks, and I brought people into the networks.

And so in the end, some of that friend hunting, which I don't think is malicious, it's like literally my voracious passion.

And that again, that's how we met this one, when we keep talking about Maria.

Because I just like so impressed with her self-discipline and her knowledge of metrics and her competence, that I think I like showed up, maybe I showed up in Chicago and was like, I'm in Chicago, wanna have dinner?

It's like.

No way, that's awesome.

But like, you gotta make the groups that you wanna be in.

Yeah.

To get the advisors that you wanna have.

Yeah.

And the thing that I've always advised people to do, I know we're talking about advisory, so no pun intended, but if you respect someone's work, if you look up to somebody who's a sales leader, an SDR leader, a customer success leader, a marketer, and you go, hey, that person at this brand is really crushing it, just send them a note.

Everybody's just a normal person, right?

And it's like whether you're currently running product at Rippling or you're currently running product at some company that no one's ever heard of, right?

Like somebody's doing something really right and you wanna talk to them, ping them.

Most people are willing to say yes to a conversation or a coffee or a drink or a lunch or whatever it is.

Like most people are just usually so blown away that you think that they're doing great, that they're usually willing to have a conversation with you.

And I agree with that and kind of disagree with it.

It depends.

Oh, okay.

Please, please focus on the disagree as you were.

I think it depends on how busy and important the person is because like some CMOs and CEOs and CROs, like you could email them and they're like 10,000 emails behind or like they're linked in.

They've just got like they're, you know, or like, oh, can you mentor me?

I'd sound three tactics.

One, I show up where they're speaking and I like sit in the front row and I like try to talk to them afterwards.

And then like one month later, I say, hey, I went to your event and I listened to you say this thing, and I'm so interested in you're doing this, and something I'm doing is related to it.

I need advice on this specific thing.

And that for me has been better than like, hey, I'd love for you to mentor me.

The second thing I've done, and in fact, there's like a funny example that's max monopolizing my time right now, but I've like had something going on.

Like often, like I volunteer to like help get some speakers for an event, and then I want to invite this person, I want to meet to the event as a speaker, and that's how I get to meet them.

So right this second, I think the pick randomly started helping Sassler organize a CML brunch for a couple of weeks from now.

And I, you know, I don't know what, I did it because I wanted to go to Sassler.

I wanted a free ticket.

I wanted to like meet people in the green room because I always meet amazing people.

I wanted to like see some of my friends who I thought were going to be there.

But then it gave me this like platform to reach out to people I've wanted to really meet, but I don't know yet, and be like, hey, I'm having this event.

And actually these amazing other CMOs who are my friends, who I sweet talked into doing it, are coming, would you come too?

And so like Diego Lomanto, the CMO of Writer, who I haven't met yet, is flying from the East Coast to come out for it because the other people were cool.

So offering them something of an exchange, that was really valuable.

And then the third thing I'll say is, I guess it's the same but different.

I just try to make it so easy for them.

I don't hit people up on LinkedIn.

I don't think I met Maria actually by staying in Chicago, but I have flown to a city before and been like, hey, I really wanna meet that person.

I'll be like, hey, I'm like at a meeting two doors down.

Can you meet for 15 minutes at this coffee shop that's right outside of your office?

Like so specific and tactical and practical and like in their space.

And then I guess back to your point, then I really nurture it.

Like with some of my best people be like, I try to make sure to talk to them like once a quarter be like, oh, how's your daughter's college application going?

And just like really create some sort of connection because that ended up making them available to me to support me, to give me advice when I needed it.

Yeah.

Yeah.

I guess my point was just almost everybody is approachable and people should not feel, they shouldn't feel scared or embarrassed to reach out to somebody.

Not everybody is gettable.

But if you make it easy and if you ask very specific questions and approaching somebody out of the blue and saying, hey, will you be my professional mentor?

It's probably going to get a lot of nos or more than likely a lot of things that are ignored.

But coming to somebody either seeing them in person or referencing their work and saying, hey, I really love what you did here.

I'd love to just ask you a question about this specifically, contextualizes it so the person is like, okay, well, they have a question about this PLG campaign I did or this SEO tactic I had or how I pulled off this really great virtual event or something like that.

But I think if you're specific in your outreach and you don't ask them for too much, I think most people are willing to have a conversation with you.

Absolutely.

I mean, this isn't, it's actually the little, it's harder, it's a little harder.

Like, I mean, like for example, you do have to have, I don't know, you gotta be relevant.

It's just like sales in many ways.

Like I get, I mean, I get a ton of people asking for my time, I take literally, and please everyone, I'm not trying to open the floodgates, but like, people have been amazed that I take 70% of them, because I want to meet people, and I learn from every conversation I have.

So, I take them.

And you know, I have a background in sales and marketing, so I get both sides.

And I love it, it's great, so I get it.

Those are people reaching out to me.

I do get another 30% where it's like, I don't know, so I feel bad if you're in that 30%.

The other thing I'll mention, though, there's things you can learn from sales.

So one, you want to say, like you guys were saying, you do want to be like, hey, I do this, and I loved your, when people come in and say, I listened to the podcast, I loved it, I'd love to meet you, whatever, I'm like, of course, you fed my ego, I'm in.

But no, but you know what I mean?

Like that tells us that we have something of a connection.

The other one that you can learn from sales is just because someone doesn't respond to you, initially doesn't mean they're not gonna respond.

Like if you take LinkedIn messages, I mean, those things go on the ether if I get another thing that week.

And so like, you know, I had some guy the other day, I'd be like, well, I reached out and you didn't respond.

I'm like, Ian, it doesn't mean I don't like you.

I mean, now I don't because you said that.

But before that, I just missed it, you know?

It's like it is important and it's so valuable.

I just think this is not the conversation that people would expect.

And it's huge.

This is amazing.

It's so true.

Anyway, sorry.

Go ahead, Carilu.

I was just going to say, I think LinkedIn has opened up an opportunity to engage a lot more with people who are ungettable because you're so surprised.

You know, you comment on their post and there's actually not that many people commenting and having a conversation.

There's a lot of liking, right?

But if you comment and then they, you know, I don't know.

I know Lenny.

I was on his podcast a year, a year and a half ago, but I'll comment on his posts and then he'll comment back and then we'll comment together.

And you know, there's some people that I don't know.

And the more they show up on and comment that I'm like looking up their profile and sometimes they reach out to me and I was like, yeah, I thought they were interesting.

They made a good point, right?

Like there's a lot of ways, like you're saying Craig, to just use sales tactics, which again aren't malicious.

It's actually like your desire to become closer to people that you think are super interesting, to engage them in a real way with real content.

And if someone's been like a smart thought partner to me on LinkedIn, I'm happy to spend time with them.

It's more like, I'm a random person in a random place and LinkedIn said you would be interesting.

Would you like to connect and hop on the phone?

And you're like, no, I'm ready, I'm not seeing my kids and husband.

I have to shrink the time window here.

Yeah, yeah, for sure.

By the way, I did see your CMO gathering at Saster.

It looks like it's going to be amazing.

And so on something like that in your story before about the sort of happy hour get together that you were involved with in your old PR days, like that's interesting too, right?

Like, cause that's there's a lot of initiative there.

Like, I don't know if you guys have been invited to AJ Gandhi's things yet, but like, yeah, I mean, that guy has is when you talk to him, he's doing a lot of networking and he absolutely loves it.

But the way he's done it has been very similar conversation that we're talking about here, but also he's put together events with other people just to, and he said, oh, I want to do a CMO thing.

I want to meet more high-end CMOs.

Can we go do a dinner?

It's like, it's amazing, right?

He's taking the initiative, creating his own sort of gatherings to go meet people.

And I think that's a, and you mentioned the happy hour, you mentioned even just offering to put together events and using that as a way to connect with people.

I think those are also hidden gems in this conversation of things that people can go do, you know?

Well, and again, I feel like I'm living in the past, but I was so hungry for that network when I was at Atlassian, and I had so many questions and I just didn't really have these people that I admired that I could ask questions to and who would call me back and talk to me frequently, that I really invested heavily there in my own personal life.

But I mean, you need these layers, right?

You need someone who is really close to you, who will get into your details and help talk about day-to-day challenges.

And sometimes this is a best friend from college, or your spouse, or your work wife or husband, right?

There's some people you take close advice from.

There's these bosses and your ex-bosses.

Some of my very best mentors are my ex-bosses because they're so invested in my career that they'll take a call anytime, connect me to anyone.

I've really busted my ass to earn those relationships.

Then there's these people that you meet at networking events who are great, and those people are amazing, right?

Jane Hines, I had an emergency once and I called her and asked for a crisis comms company, and she called me back at 6:30 a.m.

on her vacation to give me the personal mobile phone number of the best comms, crisis comms person in the country.

You can't pay for that.

If I had searched the internet and asked ChatGPT and called three people who had never used comms companies and done an RFP, I could have done all that shit, but the built a relationship, got me just what I needed, the best thing in under six hours in the middle of the night on vacation, right?

And that's one of the most extreme, but you need these layers.

So people that are your networking friends that you can count on.

And then I think there's this layer of advisors that are between your advisors and your board, whether this is your operating partner advisors, this is a hired advisor for sales, for customer support, for marketing, like really advising that C-suite level in a hands-on operational way, with hands-on operational and strategic way.

I feel like it's like a health routine.

You can't just exercise or just eat healthy or just sleep enough.

Like if you just do one, the system doesn't work.

You need these layers of people to have a really flourishing career.

Layers of people that care about you and are helping you on your journey.

That was a good run at the end, right?

Yeah.

Mic drop.

Yeah.

That was a great ending mic drop.

All right.

Well, look, we hit the time.

That was an incredible conversation.

I appreciate it.

I think everyone will appreciate it because I'm not sure it's a conversation everyone's having.

So that was awesome.

That's exactly what we want to do at The Transaction.

It was such a different topic from any of our other guests.

I think it's just so spectacular because I think that this is a place where a lot of CEOs and other operators understand that they should be doing this.

They just don't know the right way to go about it.

Advisory can be a make or break function to your business.

I think in a lot of cases, the companies that are very successful, they use advisors at the appropriate time over the course of their journey in order to get them to the next stages.

And so, running that play appropriately within a business can mean the difference between maybe not making it and having a really successful exit.

So, I think this is critical and more people should be talking about it.

I absolutely agree.

And also, I'll say that it's like so many things, you just gotta try and instead of thinking about it and analyzing them all and getting worried, I think you start with one and you try to have some sort of cancellation clause.

Like my contracts are usually structured one to two years.

They're usually one month cancellation after like four to six months together, because I do a lot of upfront work that I want to monetize before.

I give them a lot of extra hours to learn the whole business and then over the course of the contract.

But I think you try some and if it's not the right one, you flip and you try another one.

It's like psychologists or doctors or dentists, like you'll know if they're helpful.

If you are excited about the meeting, holding some things you're excited to talk about and you come up with some really good solutions or templates or benchmarks or conversations.

Or if you dread it and it's a bad part of your week, like move on, find another one.

There's lots of great advisors out there.

You might need different advisors at different stages for different things.

In an ideal world, you hire a CMO that can learn and grow in different ways, but you might really need a demand generation advisor for a while and a comms advisor at a different period of time.

I offer all because I thought you had to cross-train to become a CMO, so I've done every single function.

But a lot of the advisors I refer to are for different kinds of specific things that can help companies at a specific time.

Try it out and see what works for you.

Awesome.

Well, thanks again.

That was awesome.

That was an excellent ad.

We give some bonus around, so we really appreciate it.

Thanks for joining us for another episode of The Transaction.

Craig and I really appreciate the fact that you've listened all the way to the end.

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