S6E31 - Dan O'Sullivan - Treat outbound sales messaging like a haiku

Hey, guys.

We are already recording, Dan, because Scott usually comes into the meeting on fire.

Are you on fire? Scott?

Scott, are you there?

Damn, I can't hear you guys at all.

We.

We hear you.

There we go.

There you go. What's up, bud?

Hey. Not too much, man. How you doing?

I'm good. Good to see you. Where are you? Are you where. You look like you're on a beach.

Where are you? I'm in Fire island in New York.

Okay.

Yeah, I'm on holiday here with my family this week.

Cool. I was just glad to hear you say you weren't at Fire Festival, so, you know.

Yeah, it's so. Just chilling. How about yourselves? You guys doing okay?

Yeah, I'm. I'm home.

Yeah.

Yeah, I got. I got no complaints. I got no complaints. All right. So, Dan, I think you've done this with us before. Haven't you been on before?

I've never been on before, but.

Get out of here. I blame Scott. We, for that first time, totally Scott's fault to not do that. So. Gosh, terrible, terrible, terrible, terrible.

We're doing it now.

That's what.

That's what matters.

Yes. So, you know, the quick thing is, you know, we'll talk about anything you want to talk about. If there's something you don't want to talk about, put it at. You know, message us in the chat so that we don't go down a certain path. We are actually already recording because we decided that makes it more fun and interesting to record from the get go. You know, we'll go anywhere you want to go. At the end, we'll sort of flip it to you to. To say, you know, what questions you have for us, and we'll kind of. Kind of go from there. I think if you. I'll get your raw files if you want it, and I think this will drop on the 11th of August. So that's. That's the quick rundown.

That's.

That's for everybody listening. This is the behind the scenes stuff we talk about most of the time before we actually hit record. But we're in a. We're in a. We're in a new mode these days, baby face. Scott wants something different.

New era. It's a new era.

I know Scott's showing up without a beard and I'm showing up with one. It's.

Yeah. Completely. Completely. So before we jump in, welcome everybody to the surf and sales podcast as we slowly creep to the 500th episode. We aren't there yet.

Might be early next year before we get there, Scott, just so you know, for that's our milestone. But got to try to get there.

We got to try to get there this year.

Yeah. Then we need to hustle. We are excited about surfing sales. The next event is in October in Portugal. We are officially sold out. But if people are interested, we do not spam you just go to serpentsales.com please just put your email address in. All we do is send people when we release the next date and the next location which will be decided in the next month or so. But check us out and then please check out our friends Win AI who are sponsoring the event. We appreciate them, you know, supporting us and supporting all those folks going over there to Portugal and another.

Sponsor. Who? God, Scott, who is it? Vasco. Right? Vasco.

Right.

I'm sure they're going to love this one.

Richard, on the intro.

This is why it's fun though, because it's spontaneous and real. We make sure that it's there. Vasco, if you haven't checked out, Vasco app is a revenue architecture platform to improve your go to market speed and efficiency and it actually helps with creating real dashboards with real forecasting versus guesstimate forecasting, which is sort of how Scott likes to do forecasting, I think.

Right.

So I don't like to do forecast at all.

Yeah, exactly as. As we decided last night. You know, Scott doesn't want to be in charge of anything. He just wants everything done his way.

That's right.

That, that is Scott lease. That's his definition.

That's right. And you left out one sponsor. Provide the Slide, which is our good friend Dan o' Sullivan's company.

And I didn't know they were sponsoring affiliation.

Yes, he's a part of it. He's a part of it. Tell everybody about Provide the Slide. Let's start right there.

Sure. So. Well one, it's not a company, it's a ngo. But and I am, I'm a volunteer for this NGO and I, I assist with their fundraising and I believe it is the first charity that Surf and Sales has ever sponsored.

And so you guys were kind enough to sponsor us and help make a donation to the charity as a component of Surf and Sales Europe. And so what Provide the Slide is, is a Swiss German NGO that collects surfboards in Western Europe and it use surfboards and it ships it to currently 10 countries across the West African coast. So primarily communities that are on the coast with access to good waves and typically not no access to boards. And we're typically partnering with community development projects, NGOs in those, those places that are using surfing, you know, for different types of youth empowerment, surf therapy, female empowerment programs. And so we've been around since 2019. To date, I think we've shipped 1500 boards again to different countries. And so. And yeah, so that's what provide the slide does. And again, surf and sales has been kind enough for the European edition to, to make us the first NGO sponsor. And so. And my role there is I help with fundraising. So, you know, in the, in the context of the charity, the boards themselves are all donated, so there's no cost there. But we two of the guys who were. It's. The NGO is run by five volunteers and two of them work at a charity called VEL Africa that collects. It basically does the same thing with bikes. So they collect bikes in Western Europe and they ship them to West. And so we're able to benefit that. Usually there's like two or three feet at the top of each shipping container that can't fit another bike. So you can get 40 or 50 surfboards in there.

So anyways, we're able to ship fairly cost effectively, but we still have to fund that part in some of the other logistic fees and getting accessories for the board. So we want to make sure when we ship them they have, you know, fins, leashes, wax, a board bag. So anyway, so that's kind of what how I'm assisting them and how surf and sales is supporting us.

Yeah, it's a killer, killer cause. Killer project, I think, you know, hopefully one that will continue to support for the next few years in the foreseeable.

Where do you surf? And like, I don't even know. Like, I mean, Africa is a huge continent and of course there's multiple beaches all the way around the continent. But yeah, like, where does one surf in Africa?

I mean there's, I mean, there's incredible ways throughout West Africa. I mean, the, the charity. I mean, one of the things we may talk about, we. The it started the first place we shipped to is a country called Liberia. And there's a town within Liberia called Robertsport that's on the coast. And it basically has six point breaks that kind of lined up where you have an exposed reef break, like an exposed reef and then a sand bottom so the waves would hit the reef and stand up so you could kind of get into the wave pretty easily. And then when it hits the sand, it gets steep and so forth. Not incredible surfers. It's a great setup because you can kind of get into A wave pretty easy. And then, you know, and then later in the wave, it'll get steep and more challenging. And there's six of them. So let's say the furthest one out, if it was six or seven foot, you know, the next one would be five or six foot. The next one would be four, you know, four to five foot. So you can almost dial in which break you want. So there's incredible waves there. And that's kind of where we started. And then, you know, they're all over. We. Last year I went to Angola. Angola's got incredible waves. South of Angola, I haven't been there. You have Namibia, which has a place called Skeleton Bay, which is one of the most famous waves, considered the longest barrel in the world. We've gotten to go to Sao Tome as an example, which is an island off the coast of West Africa. Incredible waves. Ghana, Senegal. So there's incredible waves throughout the West African coast and often pretty uncrowded. And we actually, we may talk about it later, but there was a. We helped produce a documentary about kind of provide the slide in some of those communities. And we might have a link in it when the. When the episode launches. And you can kind of check out some of the waves there. But they're amazing.

Yeah, that sounds awesome. We might have to do a surfing sales.

I was just looking at, like, I'm pulling up Liberia. I'm looking at all that. Yeah, yeah, yeah.

So, yeah, that's for those. For those who don't know, you talk a little bit about, you know, how you spent the majority of your career. You've been running a major sales organization for a really long time, up until about a year and a half ago maybe or so. Yeah. Yeah. Tell everybody about your background.

Sure. Yeah. So, I mean, I would say my background in sales. I worked for a company called TransPerfect, which is a large localization services and technology company, basically translation company. And we. I worked there for 26 years. So I started in 1997 when it was about a $5 million company. And I went on an extended sabbatical about two years ago. I think when I left, it was a $1.2 billion company. So I got to kind of ride it from 5 million to 1.2 billion. And my role was, for the last 15 years was SVP of Sales for Europe, Middle east and Africa. And so I led a number of our divisions in emea and I kind of built a team for myself and no sales to a team of about 100 sales professionals spread across about 17 countries and I think we, we generated 135 million in revenue the last year. I was, I was leading it and that would be probably 90% outbound calling and mostly targeting, you know, large Fortune 500 companies and enterprise deals.

Yeah, 26 years outbounding to Fortune 500 companies.

Yeah, I want to talk about that.

Yeah, go for it.

Yeah. And then, and then two years ago I went on an extended sabbatical which I'm currently on. And so now I'm mostly, well, I'm kind of a stay at home dad, My wife works, I have a daughter, I have a 16 year old daughter that I, I help out and then I have, I work with several different NGOs and I, I do some consulting work with just like go to go to market strategy for some startups that we've invested in.

So, so let's, let's talk about going outbound.

Right.

And, and specific to enterprise.

Right.

If you had to start today, right?

Yeah.

What, well let's go, let's start at the beginning. What was outbound like for you to enterprise? What was the process like? How hard was it, how easy was it? And then where would you start today if you were trying to go outbound? Enterprise?

Yeah. Well, maybe to answer the first question, I mean when I, the way we, we approached at our company is we had, well, let's say this, I sold effectively translation services. So no one in the history of the world has ever intentionally bought translation services. Like you would save up all year to like buy your kids some translation services for their birthday. So there's no value inherently in what you, what we sold. And so by definition what we always had to find is like a business problem or a business opportunity that had a language component of it. So for example, you know, a company wanted to launch a website in 30 countries, it has to be available in those languages. If that's a strategically important thing to that company and we can help them do it, they're interested. You know, if, if, if there's no strategic need to have a language, you know, website in a different language, they're not interested. So I would say the nature of our business forced us to really focus on strateg strategic problems. Just because we needed to have that problem even to, to provide any services to, to do it.

So how do you determine, how do you determine a strategic problem at a high level? Right. Use case is always very critical. Right. To your point, if you're doing something on web, I would assume some translation in terms of legalese and contracts and stuff. Like that, like, how do you try to determine that? You know, particularly at that early stage, like now it makes sense, right? It's 2025.

You know, what we would do is, I mean, the way we would do it back then is we would open like a, like when I started in 97, I opened our Miami office, which was myself, in a room that we sublet from a law firm in a, in a fancy building in Miami. And I would basically cold call every executive in, in Florida. We would send physical letters, like literally like a letter. I would sign them and I would send them. Like every executive in Florida got a letter from me at least a quarter with, you know, like what we did. And again, mostly cold call. And so what ended up happening is actually like, if you thought about what, like when the competitors we had at that time, what they would do is actually they would target the companies that spent the most on localization. So back then, the companies that would spend a lot of money on translation would be large software companies like Microsoft that like, if they released, you know, a new update of, of Windows, they would have to localize all the different programs and all the technical manuals or big, like car manufacturers. So our competitors worked with those companies and we didn't have a lot of luck there, but we would just target every company. And what ended up happening is we found a bunch of use cases that we never would have thought of. So for example, my first big deal was with a cruise line and I had just sent them a letter and I cold called their international marketing person and I got involved to an rfp and they had a situation where they were, as a, as a strategic company, they were trying, they were building a bunch of new ships and they were, you know, trying to fill them and wanted to. They basically saturated the US market. So they knew they had to bring in gas from outside the US in order to fill the ships. And at the time, one of the biggest complaints on the ships was if you didn't speak speak English, you couldn't really follow what was going on. And the cruise experience wasn't really good. So this company was basically committing like $2 billion to build a bunch of ships dependent on a strategy that they could bring in people outside America and anyone who came on board a ship who didn't speak English had a bad experience.

So, so how do you, but, so how do you find the person? Because, you know, there's not really someone, in my opinion, I don't know, in charge of, you know, making sure everything translates into a specific language. Right.

So, yeah, so it's, it's specific to the role. So the point I was going to get at is what would happen is we would randomly find a use case, and then once we solve that use case for one of those companies, we would then roll up every other company in that industry. So we would, so we would, you know, we would just go super, super wide. And then suddenly you might hit on, you know, a random problem you wouldn't have thought of. Like, you know, as an example, our biggest division was a pharmaceutical division that did localization services for clinical trials. So if you were to run a clinical trial, you know, and you wanted to do it globally, you have to ask people questions throughout that trial, and that data, and those questions have to be 100% perfect. So if you were asking someone if they had a fever and you were supposed to ask them if they had a rash, and now two years later, you have two years of data that's incorrect, and you can't go to the FDA and apply drug. So, you know, that would be a use case I would never think of. But actually it's a gigantic use case and a huge driver. So again, basically, basically we would go wide and we would find a use case, and then we would just try to roll up every company who had that use case.

Got it.

Do you think that you want to do something, do you think you'd do something different with the strategy if you were starting today?

I mean, I think what I, I, I didn't really know this at the start, but what I came to learn is that usually you'll never, like companies have, you know, usually three or four strategies they're trying to implement that the CEO is trying to make happen, like existential crises that, like, hey, in the next three, you know, let's say 12 to 24 months, we need to execute on these three things. And if you can figure out what those three things are, which often you can, you know, if you read an annual report or you read an interview with the CEO and you can show how what you do has any vague connection to solving one of those problems, you often will get that that's the way you win. So whenever I want a big deal, that's how I want it is. This company had a strategic, like an existential problem. I was able to show that something I did might address that problem, and that's how I won. So it's a long way of saying is, if I started today, that's exactly what I would do, is I would re, you know, I would Pick five or six companies that, you know, if I win these cut, like, I always do this with my team, which is like, if you could win one company and only one company for the rest of your life, who's that company? And then once you know who that company is, like, okay, what, what do they care about? What's important to them? What is the CEO communicating is strategically important. Could I take what I do and try to see if I could, like, reverse engineer, like, what impact I could have? So, for example, if I have a product that is going to increase, let's say pipeline, by 30%, so I can even understand what their revenue is Today, what does 30% more meet for them? Have they articulated growth ambitions? You know, does it look like they have a plan that's going to guarantee that growth? Are they still looking for ideas on how to get there? And then I think if you can feed into that, some different ideas. Sorry, that's my daughter.

That's all right.

Hey, Lola. So anyway, so that, that was, that would be what I would do today. And I think actually, you know, if you look at, like, what happens a lot in sales tech, it's sort of optimizing steps of that process. So a lot of sales tax is like, how do you pull research on the, the company or the prospect? A lot of it is like, how do you do ROI analysis? Or all these different things. But, you know, the, the, the, the most important thing is like, do you have a value prop for that prospect that is specific to their roi? Like, what are the, what are the, what are the KPIs that they track? What are the KPIs they're trying to deliver on? And within those KPIs, do you have something that could, you know, affect that KPI and really trying to tie it to the way they think about it versus the way you think about it. And so anyways, that's a long answer, but that's, that's kind of how I would do it today. I would have maybe more tools to do that research. And obviously, you know, things like, you.

Know, some of that, I would imagine some of that stuff would expedite that process.

Yeah.

You know, compared to how you had to do it 20 years ago. Right.

Yeah, it would. I mean, but I think there's this creative creativity element to it that's, you know, you still have to kind of really think about yourselves in the shoes of the client and how are they, what are, what do they care about and what's important to them. And, you know, that has to come from doing, you know, deep analysis and reading a lot of company and reading their case studies and reading about, you know, the CEO interviews and their annual report and things like that. And I think you have to actually physically do that to internalize it.

How much, how much of that stuff would you include in the initial letter that you would send a company that.

I heard you, I did not oversell.

We'd send a letter and then I'd call them. Right.

So like, the letters were pretty generic, you know, like, because we were sending, you know, I would send out 500 letters a day or something crazy like that. So, but I, I would say today, like, or even when I was working, if I was to send someone an email, I might spend a day on that email. And I would treat that email like a haiku where like, I have four lines and I have to somehow boil down, you know, four pages of research into four lines. And, and I, I work off the assumption that no one reads any more than four lines. So if you can't get their attention in those four lines, you're, you're probably not going to get their attention. And so part of.

I just want to. I gotta pause you for a second. Scott, he's like me, he'd spend all day on one email.

Like, that was, that was the thing that I, that, that I heard.

And I was like, I, I saw you twitch. I saw you start to twitch a little bit.

Yeah. You know, but at the quote that I liked, the, like that I liked was I would treat it like a haiku. I got four lines. That's it. How do I make those four lines as powerful as possible? And I think that's actually really good advice for people listening.

And, and again, that's, you know, where, where you would, what, what might be in those four lines is if you had determined that, like, hey, listen, you know, the CEO has articulated that they have a 30 growth rate. It looks like you guys are going to have to generate an extra $10 million in, in revenue this year. I'm not sure, you know, if you guys have that already worked out, but we do have a solution that typically can generate an additional 30% in pipeline. You know, if you're interested, I'd be happy to talk through how it might apply in your context. But, but if you're using their statistics or their points or reminding them of something that the CEO has articulated publicly, you know, and you're using numbers, it's, you know, you can do it. It's not like every email I sent to Someone I got a response or, you know, all those emails worked, but those were the only emails that worked.

You know, like, if I get an email that's five paragraphs, I don't even read it just because, like, I just look at it and I'm like, that's. That's just too much commitment.

Too much. Yeah.

I purposely write Scott long emails so that it. I. It causes him pain.

Yeah. Yeah.

So let's talk about today.

Yeah.

Like, and I loved your point about messaging. Right. Like, treat it like that is. I mean, I think that's going to be the title of the episode. That was a great, great line. You know, even though you left two years ago, I know you pay attention to sales.

Yeah.

From your perspective, in the last two years, what are the biggest things that have made you go, wow, that's amazing, or, holy cow, that's going to be even. Make it even harder. Aside from AI and noise. Right. Like, I'm curious to. To your thoughts with all your experience.

Yeah. I mean, I think one challenge is that, like, I don't know that, like, the sales experience has gotten better. Like, if you were to think about, like, I've had some experience in my previous role and even in some stuff I've done, like, on my sabbatical where, like, I'm interacting with companies that sell, for example, SaaS software, and I don't feel like that's. I don't come away from those experiences going, like, holy, that was an incredible customer, you know, success experience. Like, I feel like, you know, you might even.

Even through the sales process, you're not even talking about customer success. Yeah.

Thank you.

After being a client through the actual buying process.

Yeah. You know, like, I feel like a lot of things, you know, you might have a demo with. You might have a call with an sdr, and then, you know, you get a call with an AE who's asking you what you covered on the previous call. And then you might get, you know, a bunch of random emails that aren't from the person who you talk to. And. And so, you know, it's a. I think a lot what happened is they tried to sort of Moneyball the sales team, like, you know, of, like, all right, we got a person who does this, and we have a person who does this, and we have a person who does this. But, you know, really, as a, As a customer, what you're looking for is someone who's just going to say, like, I got you. I've listened to you. I understand what you need, and this is how we're going to deliver that and go away and deliver that. And so I think one thing I, you know, I think AI, if anything has probably made that worse. You know, you have a lot of people who might pull research but don't know why it matters or what's important. They don't understand the big picture. And I think the challenge is, you know, how you, you do have access to all this research, but if you don't really understand why it matters or what the big picture is, like, it's hard to use it. I'm, I'm somebody who, if I can understand like the big picture, I can fit specific details into that pretty easily. But if I don't understand the, like the bigger picture, it's hard for me to do that. So, you know, I think like, I know for me personally the thing that really transformed my career was like reading like there's just books that like help me, you know. Like an example is a book called like the 10 day MBA. So I didn't have an MBA, you know, and I would often get insecure if I was pitching to, you know, senior executives and you know, afraid I was going to use the wrong word or, you know, they would say some acronym. I didn't know that was a really helpful for me thing, for me to just understand, like, how does a company work? Like, what does HR do? What does accounting do? What is, you know, what is everyone's role? What is business strategy? You know, there's a book called the McKinsey Way which is about like how McKinsey approaches engagements. You know, and that was like a really helpful book to think about. Like how did these guys who charge guys and girls who charge, you know, two, $3,000 an hour, how do they approach a CEO and interview a CEO? And so I think one of the challenges, I think people today read less and that's how I learned. So I don't know how else you would learn, but that just happened to be the way that I was able to figure some of these things out and then incorporate them into my approach. And so TikTok, man, what are you talking about?

Well, that's, that's, that's the challenge is that the sellers of today are learning in 30 second sound bites.

Yeah.

In a commitment of I'm making a number up, but like a hundred page book, maybe it takes you, you know, a week or two, three weeks, an hour, a day or whatever. Like there's prolonged sustained focus attention learning versus a 30 second sound bite. And that is a massive difference in how the new generation of salespeople are learning skills, acquiring skills and information. Not necessarily for the better in my opinion either.

Yeah. And I think depending on what you're targeting. So for me, like, typically we were trying to get like million dollar deals, you know, that know, million dollar a year deals. So to get one of those deals you really have to, you know, like it requires something exceptional to happen. You know, if you had a product that's like, I don't know, it's a $100 a month, you know, subscription and you're trying to get 10 subscriptions and maybe you have a simple ROI calculation, maybe it works. But if you're going to a company and trying to get them to give you a million dollars, you know, if that deal goes wrong, that person gets fired. Like if that deal gets screwed up and you spend a million dollars of your company's money on something that doesn't work, that's gonna, you know, that's gonna be terrible for that person. And so I think in those levels you do have to read and you do have to do a lot of outside knowledge and you do have to be able to come into a, you know, an enterprise and you know, justified giving you a million dollars and show that you're a serious person and you'll treat it seriously and, you know, you're not going to get on fire.

One of the things that I always admired about you was you have to do a ton of traveling. And I don't mean, you know, New York to San Francisco traveling. Like, I remember one time we were talking in Costa Rica and you're like, oh, I gotta go to Dubai and then I'm in, you know, Argentina and then I'm in China. I'm making the countries up. But I was like, good God, man, this guy's crisscrossing the planet. But that requires incredible depth of sort.

Of emotional intelligence, like local, local salesmanship.

You got to understand the culture, right. And people behave and think and buy differently. In Switzerland, where you've been living for a long time, versus California versus Japan and all this kind of stuff. How, how do you, how would you advise the sellers on your team, you know, to really like deeply understand so many potential different territories and, and the stylistic differences and how to approach going after some these accounts?

Yeah, I mean, well, I, I would say one is, I mean for the most part I was, I was deferential to people from those countries. So like in England, I, I moved to England in 22, 22,002 and I, I sold there for I mean, when I, and I also, by the way, I also was, I had my own clients, so I had like a $10 million book of my own clients that I met. I didn't, like, I wasn't the day to day manager, but I was a point of escalation on those, those, you know, those accounts. And so what I would do. So I, I was selling myself when I got to England, but then when I started hiring, I realized I had to get people from those markets. I mean, just linguistically.

Yeah.

So what I would do is I, I actually did this thing I called the sales farm, where I would have, I would basically hire a young person, usually pretty straight out of college from a country, and they would come work with me in London for six months and just sit next to me. So I would have like someone from France, someone from the Netherlands, someone from Switzerland, someone from Sweden. And, and they would just call all day. And so I could hear them on the phone all day because they were sitting next to me. So we could, you know, we could, you know, quickly debrief when they had a call and I would, and they could hear me on the phone as well. And, and then what we would usually do is like, when I hired them, we would figure out, like, all right, what are the top five, you know, companies in that country? Because oftentimes, if you're going into a new market, if you can win the most known companies, like, everything else becomes.

Easier, softens the landscape.

You're starting at the top down, going.

To Germany and you win Porsche, you're, you're, you're in good shape, you know. And so what we would do is kind of the approach I had, which is we would start to do research on each of those companies and I would usually just train them up enough so that they could make what I would call like a strategic cold call. So, you know, a good intro that would make it, you know, get someone open to talking to them. And then we would do what I called question rodeo, which is like, okay, just ask questions as long as you can until they throw you off the call, basically. And if, and if they did a good job of that, you would understand a lot of information about what their situation is. We would have some idea, depending on the industry, what the strategic problem we typically solve for them is. And we could, we could understand if it's real and if they have that problem. And then I would have them book meetings. And so we would go, we would say, like in a month we're going to go to Sweden and They would just focus on booking meetings for that month and we would go, you know, do meetings together. Most of the time you could kind of get away with English. You know, sometimes it would be tough or they would, they would be an intermediary. But my ultimate goal was like I would be the face of a deal until we won one big deal and then they would become the face of the deals with me in the background. And then eventually they just did their own deals. So they would, then I had, and then I had one person who had sat next to me for six months and I knew how they thought and they knew how I thought who were. They would go back to their country and start building the operation from there. And so, and you know, you definitely learn like, you know, there's definitely. In different countries it's easy, like, you know, it's easy to sell. As an American in England, it's, you know, I learned when I went to Switzerland, I had a young guy who worked for me and we would go to meetings in Switzerland and I realized immediately that like Swiss people would much rather buy from a 23 year old Swiss person who knows nothing than a 45 knows everything.

And so.

You wouldn't know that, like, you wouldn't know that until you experience it. That's a beautiful thing.

The patient, the patience of that strategy, I think is very different than what you see across most sales orgs, especially earlier startups even I can tell you.

That it was this way in the 90s. Yeah, it was always this way.

I can't imagine any sales job right now where somebody gives you six months to learn like that.

Yeah.

Not to mention move you to another country and pay for your housing ISO. Like I'm texting Scott in the back like, oh my God, this would be a dream job coming out of college.

Well, I mean, companies hire. I mean another way of phrasing that is you were an sdr, right. You were just.

Yeah, that's how, that's how I'm thinking of it.

And you happen to work in an office. So that, I mean that does happen. Obviously people hire SDRs and they put SDRs in offices together so you know.

That they don't have six months, they.

Don'T have a six month and they.

Don'T have a coach daily like that. Like.

Yeah. And also the nature of what is. It wasn't like necessarily just a product you were gonna buy. You know, we were taking over. For example, if we were translating someone's website, we had to integrate with their content management system. We had to integrate with their CRM, we had to do a bunch of different stuff to get set up. So the deals themselves just couldn't be closed really, you know, in six months. And we actually often had to generate the deal because we had to go to them and say, like, often people were dealing with translation in an anecdotal way or having someone in the office do it. So you're. There was a long, you had to kind of, you know, it took a while to build up to getting someone.

And then you'd go fly out there and get in person quite a bit.

Absolutely. Yeah. Yeah. We' try to meet in person whenever possible. We did a lot of events, client events and stuff like that. So.

Yeah, well, I got, I got a question for you.

If. Because, you know, we talk to a lot of people in Europe, right. And they always want to expand to the U.S. right. You talked about, you talked about a very unique way that you did it in, in Europe and globally. What's the advice you give to founders these days if they're based outside the US and they want to break into the US Market? Do you get that again? What. Because it's a different animal, right. As you said, every country is a different animal. And everybody, you know, it feels like they so much want to come to the US because there's just, it's such a big marketplace, which is great.

Yeah.

What's the advice you give those founders about breaking through?

Well, I would say the US Is probably like the one market I don't know how to break into because, like, I was always going into Europe. But I would say, well, I think in anything.

You know, the, should they live here first?

If you're, if you're going to sell into the US market, should they move to the US 100.

I think the one challenge in the US and you actually have this in Germany too, is there's not like one city. So for example, in Europe, it's easier because if you go to, if you're going to set up in England, you're going to set up in London. If you're going to set up in France, you're going to set up in Paris. If you're going to set up in America, where do you set up? You know what. And so that some of that's industry specific. So depending on what industry you're in, there's going to be regions of America. You know, if you're targeting tech startups, you might want to be in, you know, Austin or San Francisco. You know, if you're, if you're targeting, I don't know, oil and gas, you know. Yeah, you want to be in Texas. You know, if you're, if you're targeting financial services, maybe you want to be in New York. So I think it's, it's kind of industry specific to be there. And you know, and also having been gone from the sales game for a couple of years, I feel like it's very different. I, you know, for example, when I, when I worked, we were very focused on meeting people in person. Like, one of the things we did as a company is we would open offices, even like one or two people offices in crazy amounts of cities. I think we have offices in 130 cities. And, and the, the reason to do that is that you could meet people in person and you could, you know, clients and say, hey, listen, I'm. I'm across the street. You know, if you have a problem, I'm available to walk over at any point. You know, I'm gonna, I'm gonna be here for you and make sure it all goes well. So. But again, I think in America, the problem is where do you set up? I think hiring salespeople in America is, you know, it, it, it, it's kind of different than Europe. I think in many ways.

It's more expensive.

Yeah. And, and, and more.

Well, yeah, I think more complicated. You know, I think salespeople in America are used to being in like a sales system and, you know, have experience of one component of that system and, and very much expect to have the infrastructure in place for them to sell. You know, like, I think salespeople in America are almost like, you know, you have to build a race car and they can maybe drive it, but if you don't have a race car, you know, then they're, they're not even really.

There's, there's definitely a difference between the first salesperson you hire at a startup versus the 12th salesperson and certainly at a mid market or enterprise company. Right. Like, I agree with you, it's a, you know, the expectations.

But think about the entitled usae who's sitting around waiting for warm leads all day long, for example. Who would do that, doesn't want to prospect anymore.

I would say that. I would say the one piece of advice I could give or the one mistake I made going the other way when I started out is I had this idea that, like, I was very busy because I was, I had my own book of business. So if I hired someone, they needed to know my industry well and they needed to be good at sales. And I sort of viewed those as a continuum. Like, oh, here's their. You know, how great of a salesperson is this person? How much do they know about the industry? And if they knew a lot about the industry, I would cheat a little bit on how good they were in sales and like, view that as balancing it out. And what I came.

Sorry, go ahead. No, go ahead.

What I came to realize is the knowledge of the industry mattered zero. Right. And skill level as a salesperson mattered a thousand percent.

Yes.

We've been shouting that from the rafters for a long time. Yeah.

And it's really personal laziness that drove that decision because I was like, I can't really spend time training this person or I can't, you know, I don't have time to deal with.

Exactly. That's exactly the mistake that founders make. You know, you owned it. And you said it's personal laziness. And the founders always say, like, you know, I want somebody turnkey. I don't have time to teach them this or invest in that. What not. Yeah, yeah.

Or they.

Part of it is they don't know how to sell either.

Yeah. Or, you know, you need. So you need to do some, you know, you need to set up the CRM, you need to do some events, you need to do some marketing. And so they try to get someone who can do a little bit of all those different things. But again, if you. The hardest skill to find is like an exceptional salesperson, you know, like, there's way more successful doctors and lawyers and investment bankers than there are great salespeople. It's a, you know, incredibly rare skill, incredibly hard to find. And so, you know, I put all my focus on finding one of those people before and to find those people before they know that they're a great salesperson. Like.

Right.

Yeah.

You gotta get the rising stock of that great salesperson.

You want to get Christian Ronaldo when he's like 16, right?

That's right.

Then, you know, you know, it costs 150,000. £50 million to get him to transfer to Saudi Arabia. I was always trying to find those people super young and then get them in my system and get them successful and. And try to keep them cool.

We gotta. We're gonna give you a chance to ask us a question first. Want to give shout out to our sponsor, obviously provide the slide. Dana Sullivan, please check that out. Great. Cause what a cool thing to do to. To help people globally, which I think is really, really nice. And the empowerment side of that. Also want to Give a shout out to Vasco for supporting us and win AI for supporting us. So please support our sponsors because we could not be here without them. Dan, what do you want to ask us? You know what, you know, you're two years in your sabbatical. Do you even have a sales question you want to ask us or you want to ask us some existential question?

I didn't have anything prepped, but I'm good at questions. Well, we'll see, I guess. Well, so, you know, one thing we didn't talk about is I think I'm the. The. The. The mo. I don't know what you would call it, but the person who's attended surf and sales the most.

Yeah, I get a jacket like Saturday night live. We're gonna.

I'm like, five. I think I've done it five times. So I think a gold jacket.

He's got a gold jacket jacket.

So one question for you guys is how has surf and sales evolved? Let's say over the. You guys have been running, what, six years, five years?

This is year eight, I think. Eight, seven or eight. Yeah.

Yeah.

And, you know, from your original conception of what you. I mean, I think you guys wanted to do it because you just wanted to go to Costa Rica and hang out with your families and. And, you know, and then figure out a way to monetize that. But the. How would you guys say it's evolved philosophically? Like, do you feel like the. The intent of it, going into it and. And what you think people get out of it is kind of the same as it was at the start, or you feel like that's evolved?

I think it's evolved a little bit because the sort of growth and importance of meeting face to face, building a network, having a community, all of that really intensified after Covid.

Yeah.

You know, and people have been seeking that out in various ways more and more. So that changed a little bit. That was not a part of really, like, the initial, you know, kind of vision. And I think a happy accident of it all was.

A lot of people have come through and had, like.

Sort of life breakthroughs, if you will exist, and they come with existential crisis and they leave with some sort of breakthrough. I can think of a woman who completely overhauled her business. I can think of another woman who pivoted her business a little bit. I can think of a couple guys who, you know, got a little bit of spark of ambition to do something a lot more. We've had a lot of people come to us and say, you know, I really wasn't expecting this, but it was kind of made a huge impact on my life, you know, and to have some of those kind of pretty powerful stories from people.

Now, I feel like that that is a big part of what we're hoping to create, the space to provide for people. And I don't think that I wasn't at least thinking of it in that kind of, that, that kind of scope. Yeah, those are a couple of things that stand out for me.

Yeah, I think about, even for myself, you know, you guys, you know, at surf and Sales, you guys do the Crow's Nest. So it's like a place you can go and at the end of the night, and Richard and.

Scott hang out up there and you come and bring your questions or problems. And I remember when I was trying to go on my sabbatical, I was asking you guys some advice or suggestions. I think, Scott, you said two things, which was hire your replacement and document everything.

Yeah.

And I ended up taking that advice. I actually wrote like a 200 page manual, gave it to us.

You sent it to me to review. Yeah, yeah.

And. And it ended up being super helpful because actually it forced me to actually think about, like, all right, what is it that someone would need to know if I, if I wasn't here, you know, or what, what do I get questions on? And it really smoothed the way for the transition because it actually allowed me to show like, hey, you know, it's on page 52. It's on page 54.

The playbook. Yeah.

I would say that was a personal example of just some random thing that happened in the Crow's Nest that ended up actually being a facilitator to allow me to, you know, kind of go on my sabbatical. And I would say in a way where I felt like I had, you know, I had given every. I documented everything that I. No, so there's not, you know, it really made it easy to, to step away. So I'm thankful for that.

And also, you know, I would say, like, as someone maybe just to do a quick surf and sales plug, you know, as someone who's gone five times, you know, some, some of the things I've gotten out of it, I mean, one is just the surfing aspect of it. So to have an excuse to go surfing and get to surf every day, you know, is. Is great. And, and one challenge I have as a 53 year old is like, I can surf for three hours, basically, you know, tops. And then, you know, you have the rest of the day with nothing to do. So, like, with surfing sales, it was like you got to surf, you know, as much as you could surf, and then you got to have, you know, exposure to this great content. You know, at my company, because we hired a lot of young sales people, I didn't get a lot of exposure to salespeople in other contexts. And one of the powerful things about surf and sales is, you know, you get to meet, you know, 15 sales professionals at different companies and different industries and doing different things. And then also it tended to be a diversity of level. So you get people who are SDRs or BDRs, but also people who are SVPs of sales. And like, for me, you know, it's hard for me to have candid conversations with junior people on the team because you're just, you know, if you're the senior person, you know, skews everything because they, they don't want to tell you, like, exactly the truth, where if you get to meet someone, an sdr, bdr, who's, you know, you don't really know, and they're going to be super candid with you, you really get deep insights into how different, you know, generations of sellers are thinking. You learn a lot about sales, tech and, like, what different products people are using, what's working well. So it's been very powerful. You know, for, for me, it was a, a great asset that I, I originally signed up just because I was looking for an excuse to surf and then ended up being something that actually got a, a lot of other benefits.

So, yeah, we all wanted to go surf and have a little vacation, and it turned into something bigger and better and a little more special.

Yeah, it was, it was an experiment by a couple of guys who were like, let's try something crazy and different and see if we can pull it off. And we did. And it just created, you know, and we did all this pre Covid. Right. So we did this in 2018. And, you know, I remember where we started, the baseline was, as Scott always said, was we want to create something smaller that is intimate, where you get to know people. And that translated eventually into what I called the in between moments. Right. It's, it's. You're not just out there surfing, you're sitting out there with three or four other people waiting on the wave. So you're having these conversations, business life or whatever. And then to the point that you brought up Dan, you know, there are these other moments outside of the content and outside of the surfing, where you just get to connect with humans on a different level. Right. And that was. I think that was our intent. We didn't know how to articulate it quite that well other than to say we just wanted something that wasn't in a big city, in a hotel conference room.

Yeah, right.

We knew we needed. We know intimacy was needed at that human to human level, particularly because sales is such a lonely existence. Right. It is a team sport in many ways, but ultimately you're still responsible for your number. And this was a place to sort of combine all that together. So I think that was everything. Everything Serpent Sales has turned into has been 80% more organic than it has been strategic by us. Would you say that's fair, Scott?

Yeah, that's definitely fair. A perfect example is most of the reason probably that we're going to Portugal and having the event in Portugal is because Dan is volunteered and spearheaded all the, like, boots on the ground stuff, you know, the area and doing all that. Right. So, you know, we, we have Dan to thank for the first Euro summit.

Yeah.

Do we have time for one? I. I have one more question for you guys if.

Yeah, let's do it.

Okay. So I'm a big book guy, so I would say I'll ask each of you what would be your. If you could recommend one book from a sales perspective. It doesn't necessarily have to be a sales book. It could be a general business perspective. And then if you were to say one book from like a personal, like, you know, life perspective. Like, hey, if I. If I could get someone to read one sales or business related book and one personal, like, development book, which would be those books.

Wow.

So I, I kind of. I have a hard time differentiating straight up business books from lifebooks because I feel like the lifebooks are as much about business as they are life. Right. I mean, sure, you could go read the little black book of sales or Red book of Sales and all those things and never split the difference or, you know, the seller's journey or addicted to the process. Right. We might as well plug our own books. Right, Scott?

Why not? But the two books that I think have meant the most to me in the last couple of years, one was Green lights by Matthew McConaughey, because it's not about him being a movie star. It's about moving through life and how you do that. And he gives some great examples of context. And then the other book that.

Hint, hint, Scott should read is Just Let Them, which I think is a great book about understanding. We all say control what you can control, but nobody teaches us how to do that. And how to. How to navigate the emotions of that. Because we can say, well, I can't control it, but it helps you understand, well, how do I navigate my own emotions around what I can't control? Because that doesn't mean it doesn't frustrate us.

Right.

And so it acknowledges that side of it. So those are the two books. The Just Latvian one is my latest and favorite that I've read a couple of times.

Nice. God. Addicted to the process.

Yeah, addicted to the process for sure. That was the most memorable since I wrote it.

I think about. I'm like a simplistic reader in the sense, like, I don't really like reading a thousand page book. I want to get in, get out. What was a couple things that I. That I learned.

And I like to learn things that help me discover stuff about myself. So there was two books about habits, atomic habits, which everybody has heard of. There's another one that is less popular called the Power of Habit.

And these two books helped me sort of understand some of my patterns and how I form them and how I could recreate new patterns. And it's been very valuable to me over the last few years with all the different life changes and everything that I've. That I've gone through.

And then a real, real simple book which is great especially for people who have a sports background like me, is called Toughness. And it's written by Jay Billis, who's a college basketball analyst. And he talks a lot about Duke and their history there and everything. And it's just a real simple concept of, you know, how to be gritty, how to be resilient, how to be. How to tough it out. And I. I think that those are. All of those books are helpful both for sales and for life. Yeah, I would tell people to look at those.

Nice. Cool. All right.

What are your book recommendations? What are you reading?

I mean, I'm reading all kinds of crazy. I'm. Well, I'm reading a book about Mickey Dora right now. He's a famous kind of rogue surfer. And then a book called the.

The Fall and Rise of Great American Cities. It's like a famous book about that kind of stuff.

I like.

I'm.

I've been.

I'm deep in this people's history of the United States. Yeah, look, I like that kind of.

Rise and fall of, I would say myself. I mean, there's a book called like the Ma. The Magic of Thinking Big, which is a. It's kind of a book about like goal setting, but it's Kind of transformational in my life. And then I think at a personal level, there's a book called Authentic Happiness, which was written by a guy named Martin Seligman, and he was like, the head of the American psychiatry association for 30 years. And. And basically his distinction is, like, when he got into psychiatry, instead of studying, like, mental illness, like schizophrenia, he studied happiness, like, clinically for 30 years. And so it's like, basically an analysis of, like, clinically, what is the things that make you actually happy. And. And so it's a. It's a very good way to kind of understand, like, how happiness works and how life works. And so I. That was one of my books that I. I most recommend.

Yeah, cool.

Well, thank you, Mr. O'. Sullivan. We appreciate it. Where can people get a hold of Provide the slide? Is it providetheslide.com? what is it?

Yeah, maybe. Well, maybe I'll do a quick plug. So, you know, one of the components of the. The Surf and Sales sponsorship is we've. We've committed or Surf and sales is committed to match any donations to Provide the Slide by up to $5,000. So anyone who's interested in finding out about. Yes, you can go to providetheslide.com and it shows all the partner destinations. You can donate on page. There's also a documentary that will be released in early September on Apple TV and.

Amazon prime, which is kind of about kind of what the charity does. And. And, you know, again, it focuses on Liberia as one specific community, but it kind of shows some of the impact of those boards. And so hopefully in. In early September, people can check out the documentary online. And as I say, if you want, you can go to providetheslide.com.

Definitely check it out.

Yeah, we can't take boards in America yet. We don't. We don't have infrastructure for donations yet, but people can't support financially and, and hopefully one day we'll. We'll come to America.

That's awesome.

Well, it's been a pleasure, man. Good to see you and.

Yeah, we'll see you in a couple months, Dan.

Absolutely. Yeah. Thanks for having me. Looking forward to.

I think we're 10 weeks away, maybe 11 weeks away from.

Oh, my gosh. Getting close. Start working healthy, everybody stay healthy before we go there.

Yes, that's. That's true.

All right, Dan.

Good to see you, bud.

See you guys.