Episode 8: Scott Leese

Episode 8: Scott Leese Featured Image

Join us in this week’s episode as we sit down with Scott Leese, a distinguished sales leader and four-time founder renowned for his dynamic approach to sales strategy and content creation. In a candid discussion, Scott unveils his journey from leveraging LinkedIn as a powerful networking tool to hosting the innovative Surf and Sales Summit. Dive into insights on evolving customer engagement, the art of authentic connection, and the delicate balance of efficiency and personalization in sales. This episode is a must-listen for those eager to learn about transforming sales processes and the integration of professional growth with leisure.




Cross: Hello and welcome to 73 and Sunny, the podcast about the journey of getting things just right. We talk to tech sales and marketing leaders about how they’re growing, dialing in best practices and getting closer to that sweet spot. We are honored to have the opportunity to speak with our guest today.

He’s a four time founder and sales consultant. He’s written three books on sales, host the annual surf and sales summit in Costa Rica, and has over a hundred thousand followers on LinkedIn. Please welcome Scott Lease. Hey, Scott, how’s it going, Daniel? How are you? So well, thank you. I appreciate you coming on.

I should say, first of all it’s not 73 and sunny in San Diego. It’s like one of the days of the year that it just pours rain and it’s miserable. So we are nowhere near that sweet spot today, Scott. 

Scott: Neither am I, man. It’s actually been pouring rain in Austin, Texas today. So we’ve got the same thing going on.

Cross: Fair enough. I invited you on the show because you’re a prolific content creator on LinkedIn. I’m sure your other places too, but that’s where I see you. And so I really wanted to have you on to talk about insights into sales and revenue generation. Do you want to start with, where you came from and how you got into content creation?

Scott: Yeah, I actually got started with it essentially as a recruiting tool for myself. I’ve been a head of sales, VP of sales, whatever you want to call it, six times over the years and had offices all across the country, different geographies and whatnot. And years ago I got tired of paying for job ads and the struggle to recruit in these different places, which is a challenge for everybody.

And I thought I just need to grow my network as big as possible. So I know every single salesperson in San Francisco and New York and Chicago and LA and San Diego. And I just would go into each kind of micro system inside of LinkedIn and try to connect with everybody in this particular city as that I could.

And then the thesis was when I need to hire somebody, I’ll just. Make a little post that says, Hey, I’m hiring for an account executive. I am hiring for a sales manager in such and such location. And then bang, it’d be a lot easier. So that was how it started. It was through growing the size of my network specifically to save money and make recruiting easier.

And from there it grew into maybe I’ll share some things about sales. Maybe I’ll share some things about sales leadership. Maybe I’ll share some things about going out on business on my own whatever the topics were. And, you start to open yourself up a little bit, be vulnerable, get creative, write some things and, you get feedback and that feedback.

If it’s positive propels you forward. And so that was where the journey began. And, I think I probably started with that strategy around 2011 or so, but really didn’t start creating content real hardcore until about 2016 or so. 

Cross: We had Josh Braun on. Two episodes ago. So go back and check that out.

If you’d like to listen to it, he’s a really interesting guy, but also a LinkedIn kind of sales influencer. And one of the questions we had. Was around how he comes up with every, with a new post every day. Do you have a strategy? He had a list of, he was always, he was like a story gatherer.

So he was, he takes notes wherever he goes to try and, remember and link, remember something that happened to him and link that to some lesson that he wants to talk about. Do you have some strategy of posting or do you just wake up with a, with an inspired mind? 

Scott: No, I don’t have a strategy and I am not in any way suggesting that’s the smart or wise way to do it.

But I don’t, I have always just operated with I wake up today and what’s on my mind? Was it something I thought of on my own? Was it a conversation I had yesterday or early this morning with Daniel? Or something I’ve been struggling with, or, people have been messaging me about that.

I should talk about. And if I had something interesting to say, I would say it. And if I couldn’t find anything interesting to say, I just wouldn’t say anything. So I feel like there is an element of, kind of creativity don’t call it an audible kind of every day or improvisation and whatnot.

But I will also tell you that it creates a tremendous amount of stress for me, because the first thing I think of when I wake up is what am I going to write today? And the burden and pressure of that is very real when you’ve been doing this for as long as I have. And, people are expecting you to.

Be brilliant today or write something funny or creative and sometimes I don’t have anything to say at all, and I’m just not one of these people that can go lock myself in my office and write content for the next 30 days and just schedule it out. I just don’t operate that like that.

If the, if inspiration hits, I have something to say. If not, I’m absent that day. 

Cross: So this this. recollection back to a post. I don’t know how well you would remember the things that you posted if they’re coming off the top of your dome every day. But you wrote or you posted that the traditional sales playbooks might be missing the mark.

The struggle to connect with prospects is real and it’s impacting the heartbeat of growth. Authentic customer connections. So I wanted to ask first, maybe if you don’t remember it, I’m glad I refreshed your memory. All right. What do you think is changed about customer engagement? That’s causing this lack of authentic consumer connections 

Scott: are insatiable drive for efficiency and growth at all costs because you’re trying to always do more with less and squeeze more with less and you just end up moving a little bit carelessly and a little bit thoughtlessly at times.

We used to go back a hundred years, business got done in person and you met with people and you built relationships and then some deal was struck and then it involved to, I better fly to San Diego to close this deal with Daniel. And then we’re just like we can do all of this on the phone now.

And then from there we evolved to, I actually, I don’t even think I need to talk to Daniel. I can just email him back and forth a bunch of times. And then we got real smart and built tech around these tools because making one phone call at a time wasn’t efficient enough, Daniel, we need a power dialer.

That can call 20 numbers at the same time. And when somebody answers, we’re like, Oh, Hey, which one were you? And then we built these tools for email, these spam cannon tools, where we could just load all these email addresses in and create this like minute personal, personalization of a message.

And we’ve sent all these emails. And what we did was. We have come damn close to killing off these channels entirely because I don’t know about you But my ringer is off all day long It automatically goes to voicemail if it’s not a number that I recognize my voicemail tells you I literally don’t check my voicemail.

So you got to text me right? I’m not answering the phone I barely even answer the phone of my parents Or my friend’s call, let alone a stranger. Yeah. And I’m not responding to emails from total strangers or spam messages or solicitations. I don’t, I feel like I don’t have time in my day. And we get dozens of those messages every single day in email.

And now we get them in our DMs on LinkedIn as well. So we have poisoned the well for ourselves a little bit and gotten away from what works at the heart, which is really understanding what’s going on with your prospects business. Asking the right kind of questions, listening intently, having built a relationship with them over time.

So there’s some level of inherent trust there. And then helping somebody understand how you can solve this particular problem. That process has been deemed too inefficient and too slow. So that’s what I was talking about in that post. I remember writing it. I couldn’t tell you if it was from one month or one year ago.

Or whatever it was from, but I do remember it. 

Cross: It’s, not paradoxical, but it’s ironic in some ways that what was that now that you have to focus on. Doing your research and finding out, rather than blasting a thousand people, the only way you’re ever going to get a response is by doing legitimate research and looking into, what problem you might be able to solve and then finding the right person who would solve that problem.

And it really, it’s very, you have tools now, but the task is not small if you really want to get something answered too. But all of that research could go to waste because you’re using a channel via email that’s and so I, I wonder when you go into your consultant, I’m sure people call you in and say, Hey, open up their trunk and say, tell us what’s wrong.

And, open up the hood and tell us, what are we missing here? What’s going wrong? Why aren’t salespeople being successful? Is engagement one of the things that you look at? What are, what are you looking for in terms of outreach? Cause I’m sure that’s one of the big questions that the sales team saying, Hey, we’re not able to get in touch with people.

What should we do? What’s your answer? 

Scott: Yeah. As far as outreach goes, there’s really two things. Number one, people typically don’t have a process that they follow. So they’re just haphazardly all over the place. A little bit of this I better try that other thing. And then they try that other thing and, no, two, no, two pitches sound the same ever they don’t demo the product the same way they make five calls one day, 45 the next day, haphazard scattershot kind of thing.

So the lack of a process is. Almost always inherent in these early stage companies that I typically work with. And the second thing is they just don’t take advantage of all of the different channels that are out there. So there’ll be two email dependent or two phone dependent. And they’re not doing stuff like utilizing a kind of referral and partner channel, nearbound kind of approach.

They’re not utilizing video. They’re not utilizing social. They’re not playing the long game and connecting with people on different social platforms and engaging with their content and slowly over time, waiting for a little bit of rapport to show up and then saying, Hey, Daniel, I saw you posted this thing the other day.

We actually solve for that, man. If you ever want to talk, let me know and just slow playing it there. So that’s what it is they’re just too heavily invested in one thing and they ignore the others. And I think that we’re in a buying situation now. We’ve got lots of different kind of demographics in buying positions and everybody has their own preferred method of communication and we don’t know which one is right for which person, right?

So if you are trying to sell to my parents, they’re telephone people still. They talk on the phone all day long. Me, I actually, the easiest way to get ahold of me is to text me. That’s going to get you the fastest, best response. You might be an email guy. Someone, somebody else might be a, LinkedIn DMs person.

Somebody else might be a snail mail person. One of my good friends Dale DePriest sends these super creative snail mail, letters, and he has all these campaigns around all this kind of stuff. You’ve gotta try all of those things, basically. Until you figure out which one is gonna work for this particular opportunity, I better stick with that channel.

If I’m telling you should text me, you should keep texting me. You shouldn’t suddenly try to email me. Those are the two things, not diverse enough in terms of the approach, and then just not having a process in place. Those are the two biggest problems. I think 

Cross: it’s interesting. You bring up early stage because I would imagine that’s where the chaos initially exists, but.

It’s also interesting because we work with a lot of enterprise level organizations, the same, and it’s like the problem with scale, right? If you start off with broken process, as you scale, it just gets more broken or, it, it breaks at scale. But we still see the same kind of things in like enterprise level organizations, like when we talk about engagement strategy or outreach strategy, they go, there’s more people there’s like interdepartmental collaboration where marketing’s talking with, Engagement analytics, and there’s data folks, and then you ask them, so what do you do when a lead?

Comes in if you get a new inbound inquiry, what happens? And they go like Jane, do you want to answer that? And then Jane, it’s an email goes out and then, Hey sales, what are you guys doing? It’s oh, sales makes a call. And then you’re like how many? And you go it depends on who it goes to.

And you know what, where you would expect that smaller organizations would have these issues. Cause they’re just trying to build, but sometimes you go into these large organizations and there’s more people, but the chaos exists. It’s the same, it’s just at a bigger level. 

Scott: Yeah. That’s been my experience as well.

And you, you ebb and flow between having a stringent process in place and then nothing and loosening the reins a little bit, and then you’re like, Oh, we’ve lost control. We got to tighten everything up. And then we tighten things up. And then we got to loosen them up again. Cause people feel restricted.

It’s just like back and forth thing. And so I think, most sales orgs and most companies are going through that exact experience, nobody has it dialed in perfectly for very long, that’s been my experience. 

Cross: That’s interesting that you noticed the ebb and flow, because I think that’s certainly true.

It just 

Scott: goes to show that you can never stop paying attention to it. You can never stop thinking about it and making sure that you’ve got it dialed in. It’s not like you just fix it one day and you’re like, yes, this is fixed. I never have to deal with it ever again. It’s this is a lead, a living, breathing entity.

Things are always changing, always evolving. We’ve got to be tinkering this, tinkering with this, evaluating it, making sure it’s being followed. Think about people going in and out of the organization too. So people who were very good at following all this process, leave for whatever reason, people come in new to the organization.

They’re not good at following this process or they come from a different process and they want to do it the old way that they’re used to, right? So it’s this thing that’s got to be evaluated all the time. You can’t just set it and forget it. 

Cross: How much do you get into tech stacks with your consulting clients?

And is there a piece of tech that’s like a sales must have that you think all sales and revenue teams should get? 

Scott: We go, we get pretty deep. My, my partner, Jean Marie Wilkie, she handles all of the operations and tech stuff in our consultancy. So she’s usually diving in with people there.

There’s the obvious stuff. I think like you probably need a CRM. That’s probably a must have, right? Which one you use. I don’t really care, but you should probably use one, right? Then you’ve got to have leads from somewhere. You’ve got to have some kind of data. Who am I supposed to call? I think if you’re making, if you have no list and you’re making salespeople scour the internet, creating their own lists, that’s, 1995 called and wants their strategy back.

Again, which data provider? My experience is. It’s completely different. The the accuracy of the data and the experience from one company to the next, Daniel and I, we use, we, we both buy zoom info. We sell to two different segments. I love it. I think it has good accuracy. And you’re like, this is the worst tool ever.

So you go use, some other one seamless or whatever, and the experience flips. So don’t really care which one, but you got to have. Lead list of some sort and you probably at this point, you need some sort of coaching, tool, some method to give and receive feedback, to listen to calls, to, hone in on certain parts.

Of calls that are problematic rather than having to listen to the whole 45 minute demo. So that’s conversational intelligence stuff. Do you still need an engagement platform, a sales loft and outreach type of thing? I think for the last 10 years, people have been like, yes, that’s a must have top four must have.

Now people are maybe like, I don’t know, because nobody responds to email really anymore. So do we really need it? So those are like the, tried and true kind of platforms and pieces of tech stack that you need. And beyond that, everything starts for me to get real into nice to have stuff. I don’t, I’m not somebody that thinks you need to have 20 pieces of tech.

I came up in a world that had nothing. I know it can be done without it a little bit. So I think you just have to make sure that whatever tool is being utilized by the company is actually being used appropriately by everybody there. If you’ve got four pieces of tech and there’s 50 percent adoption, adding a fifth tool is not going to help very much.


Cross: the, that one of the most common things we would hear when we first started working with, especially, so we come from the real estate and mortgage world and everybody’s running like independent businesses and the most common thing you, when you’d ask. What, what CRM are you using? And they would say I’ve got three.

I use this one for scheduling and I use this one for X and the company gives me this one and I don’t really blog into, I don’t really log into it. And I’ve never, I don’t use it much. And it’s, it feels almost like a diet in some ways where you just, you’re prescribing something to someone.

It’s if they’re not, if you don’t get them onto it, it’s just not going to do any good. So I know that it’s more high adoption with a lower amount of tech is better than the reverse. Hey, I wanted to talk about, because one of the first things that. I noticed maybe one of the first times I noticed you on LinkedIn was when you was because you have that emoji in front of your name on LinkedIn.

And this is one of the most brilliant things. I think I told you about it when I reached out to you. But one of the most brilliant things you’ve done, which is put the emoji in front of your name so that when people. Reach out and it’s one of the merge fields. Instead of saying, hi, Scott, it says, hi, like surf emoji guy and, to ignore it, or at least to give context to it.

And then after looking through your profile, I saw that you do this surf and sales summit. I wanted to ask about it. Who’s it for and why is a surf and sales summit the most brilliant idea for a sales conference ever?

Scott: I don’t remember when I put that surf emoji in there for the first time. It was years ago. Now it seems so common place now that everybody uses seems like something like that, but yeah, that was why I wanted to catch, I wanted to figure out what was a real person and what was a bot sending me some kind of automated message.

Why is the surf and sails summit the best experience out 

Cross: there? I just think it’s brilliant that you would combine, cause conferences are like they’re in Vegas and you’re walking, you’re walking from air conditioned room to air conditioned room. The idea that you would have surfing involved with the conferences is in my opinion, 

Scott: that was the idea.

First of all, I’m not somebody that enjoys going to a conference with 50, 000 people there. That’s not my scene. I don’t, I’m not like super outgoing, party animal type person walking up into booths and saying, Hey, I’m Scott. Who are you? That makes me very uncomfortable. My social anxiety like goes through the roof, but you get me around 15, 20 people.

And I’m fine. Normal, right? Excited, even. So the original idea was, why do I have to go to a sales conference with so many people? Why can’t we do a small one? So instead of just barely meeting all these people and never talking to them again, I actually spend about a week with 20 people and I really get to know them.

And maybe I can help them. Maybe they can help me. Maybe I teach them something. Maybe they teach me something. And then it was, why do I have to go to the conference room at the Marriott in St. Louis, Missouri? I don’t want to go there, I, all of those places as a venue are just so stale and boring.

I don’t want to be there. And I’m taking time away from my business, taking time away from my family. It’s if I’m going to go do something like that, I want to go someplace cool, right? So I was like, how come nobody has a conference in a cool place like Costa Rica, on the beach?

And I don’t want to sit and listen to people drone on for eight to ten hours a day, like Why can’t we do three or four hours of content a day, walk at the beach, surf the beach, give people surfing instructions who don’t know, how, have drinks, have food, maybe go on a zip line tour, look at sea turtles, like that sounds way more my speed where it’s like half learning, half vacation, small group of people, but it’s an experience and you come out of that experience with 20 friends.

Yeah. And colleagues that you maybe will work with one day, maybe who helps steer you the right direction in your business or your career, maybe they’ll hire you one day or you’ll hire them. Maybe you close a deal with one of them. Cause one of them was in your buyer ICP your profile or whatever.

And everybody who’s come to these events over the last, I guess it’s been six, six or seven years now. Everybody has like amazing feedback for us all the time. They’re like, this was a life changing experience. This is how sales conferences should be done. I learned a ton, I networked a ton, but I’m also refreshed and I had fun and.

So for me, I used to live in Northern California and I used to surf, a couple of times a week, three, four times a week before I had kids. And then I moved to Austin, Texas. You can’t surf in Austin, Texas. So I had to figure out a way to, to scheme a couple of surf trips every year, essentially.

And make a business out of it. So it’s I got to go to work. I got to go to Costa Rica to go work. So turns out that this kind of. Goofy idea is a hit with a lot of people. And yeah, we’ve had a good run. We expanded and built a podcast out of it.

I’ve done a golf and sales event as a spinoff of surfing sales. And now you see more and more people creating these micro events and recognizing the power. And I think that’s a good thing. 

Cross: Yeah. I’m only thinking of what other activities that I enjoy that we could turn into conferences. 

Scott: We could easily do it.

Cross: Literally I’m as anyone who knows me I’m somewhat of a pot of a pickleball addict and 

Scott: I’ve had multiple conversations with people about creating a pickleball and sales event, like a tournament, whatnot. Yeah, that’s there. I’ll help you do that if you want. Okay, 

Cross: let’s do it. There are certainly enough.

Pickleball just going to the, to where I play regularly. The park is close to a business meeting. We talk about everything. There’s exactly, there’s a lot of downtime and you get into conversations. 

Scott: Now let’s say that you run A real estate practice brokerage or whatever, right? And so you decide, you know what?

Let’s host a local like pickleball tournament slash meetup. So you get people from your industry to show up. You get your lender to show up. You get the title insurance person to show up. Everybody who’s associated with the transaction in some capacity. You get a couple people to sponsor the event.

Keller Williams sponsors this thing. So and so sponsors this thing. Everybody’s there, right? Now you charge, I don’t know, let’s call it a hundred bucks entry fee for the tournament. All of a sudden, man, if you get a hundred people paying you a hundred bucks, that’s ten thousand dollars in entry fees. Maybe you made another ten thousand dollars in sponsorship fees.

You got twenty grand. The venue probably is not going to take very much of a cut in my experience. I did some research on this. They don’t ask for very much, right? So not only could you throw this event, which would be a great time, you’d be able to network with all these different people who may or may not want to buy or sell a house now or someday.

You capture the lead list. Of all these people because you’ve got all their information on the entry fee, right? They are networking with each other. So you’ve got the long tail possibility of you making revenue off of it. And in the near term, you just made yourself five figures plus for the weekend.

That’s essentially the surf and sails model, but applied to real estate and pickleball. 

Cross: And you gave it all away here on the you’re on the, the 

Scott: model, the model works really well for things that are free or cheap. When you think about surfing sales, I don’t have to pay for access to the facility because the ocean is free.

Pickleball. Okay. We got to get courts, right? Our golf. When I did golf and sales on it, we got to pay green fees. I have people hit me up for seven years now who say you’ve got to do one for snowboarding, snowboarding and sales, skiing and sales. I’m like, yeah, but the math doesn’t work because the lift ticket is like super expensive and the lodging at these places is super expensive.

So there’s ways to do it free and cheap and easy, right? Pickleball is relatively inexpensive. Imagine you did cycling. Everybody brings their bike. You just go for a ride or you go for a run. If you’re a runner. Oh, it’s an interesting model. The pickleball one has been explored before. I’ve gotten close to executing it a couple of times, but I’ve yet to do it.

Cross: It’s ripe for exploitation for sure. 

Scott: Yeah, there you go. 

Cross: And I may hit you up about that after this, but for now, thank you so much, Scott, for joining us. It was extremely generous of you to come on. Please follow Scott Lees by one of his books. Consider attending the surf and sales summit in Costa Rica, or consider attending one of his other.

Or the pickleball coming to you soon, the pickleball sales and summit sales summit. Anything else to plug Scott? 

Scott: No, that’s it. Maybe if anybody listening is, in this kind of like early stage, trying to take their company from, 1 million to 25 million kind of growth phase, that’s my specialty.

I’ve worked with hundreds of companies over the years. Somebody ran the math the other day and I think I have like a. Almost one in five record of companies who are getting acquired, which is pretty high over the over the norm. Anybody who’s looking for help in that department, that’s my main job and would love to talk to you.

Cross: Awesome. Yeah, absolutely. Reach out to him. And for us please and subscribe and go back through our old episodes to get more nuggets of wisdom from sales and tech leaders for this episode. Thank you very much for being here, Scott. And thanks for listening to 73 and Sunny. Thanks man. Appreciate it/