AI Sales Systems: 4 Daily Actions and 43 Agents | Simon Severino

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Simon Severino runs 274 workflows and 43 AI agents. He still starts every day with just four actions.

I've got sticky notes. Pink ones, yellow ones. Five sheets of paper buried on my desk. Simon counted twelve on camera. He's not wrong.

Simon Severino is the author of Strategy Sprints and, with Jay Abraham, Time Freedom. He's served entrepreneurs for 23 years, and he's built a sales operation where AI does the boring 90% and he does the 10% that matters.

His rule stuck with me: "If you're doing it twice, make it a system, make it a template, make it a checklist."

What you'll learn in this episode

• The 4 daily "boat movers" that replace a desk full of sticky notes
• Why he asks hot leads for a mobile number—and what it tells him when they refuse
• His Claude Code "refinery" that turns one 10-minute video into nine pieces of content
• The Seven Critics: why every email runs through 8 to 9 quality checks
• Raise the floor, not the ceiling—why systems beat goals when the day goes sideways

The best lines from Simon

"Your time is limited, but your impact doesn't need to be."

—Simon Severino

"I don't raise to the level of my goals. I fall to the levels of my daily habits, of my systems."

—Simon Severino

"I don't lead with AI. I only have AI add like four more arms to people."

—Simon Severino

Like this one? You'll also like Anthony Iannarino and the only sales guide you'll ever need and St John Craner on selling big-ticket tractors in rural New Zealand.

Full transcript (lightly cleaned)

Skim the chapter headings and jump to what you care about.

0:00—Why listen to an Austrian about sales?

Wes: Simon Severino, win more deals at the prices you want, author of Strategy Sprints. Welcome to The Sales Podcast, man. All the way from Austria. How the heck are you?

Simon: Hello Wes, thanks for having me. Hello, everyone.

Wes: So why do I need an Austrian to tell me how to sell I'm The Sales Whisperer, man. What do you know over there that I don't know?

Simon: Probably every good salesperson knows already everything that they need to do, right?

Wes: There you go. So they should just listen to me, right?

Simon: Maybe a few things are changing in terms of what AI is doing. Maybe. So we can explore that.

But really, I think everybody listening, especially if they listen to so many episodes of yours, they know what's needed. They know what's right to do. They know how to do it.

So what can we actually bring from Austria? Maybe just a little reconnection to what they're doing and reminding them of how capable they are and how easy it is actually to fill pipeline if they want to.

1:06—Working with Jay Abraham

Wes: So talk me walk me through this, right? So you've written a few books. Well, how was it working with Jay Abraham?

'Cause like I've liked that dude for a long time. Is he good to work with?

Simon: A legend. A legend in the field. I've been reading his books for like 10 years, listening to his master classes, applying the thing, especially the joint venture model, that you can always find somebody who has a resource that you can leverage, and you probably have assets in your business that you are not leveraging yet, but you could.

I think that's his genius. And when he came on my podcast. We hit it off and then afterwards we started a program together.

That program was so helpful in creating breakthroughs. So entrepreneurs would bring us big problems that they have, like a sales problem, a marketing problem, a pricing problem, a hiring problem. And then we would live, work on that, break through it.

And that program was so beneficial. That we said, how can we bring this to even more people? Even as fast as possible.

And that became the book Time Freedom, because each chapter is one leverage point that you can apply to your business so that you can have more impact without putting in more time. Because your time is limited, but your impact doesn't need to be.

2:31—Why we don't do what we know we should

Wes: Well you know, I pulled up the quote you know, Saint Paul talks about the spirit is willing but the flesh is weak. So even though people may know, like we don't do the things we need we know we need to do, you know, should floss more often, you know, eat more salads. Do more prospecting, but we don't do it.

Why don't we do it? Why don't we do what we know we should be doing?

Simon: That's right. That's right. So yes, let's start there.

Cause this is really reconnecting us to the work that we have in front of us and we know exactly what we should be doing. So what is in the way actually? Let's go one blockage after the other.

The first one is having a plan, the second one is executing. So let's start with the plan. Do we when we say I know I should do more prospecting.

Do we have a clear picture of what the action is? What is the action? Is it calling somebody who?

Calling people that were past clients, calling people who are potential partners. Is where do you start? Or is it emailing? Or is it sending mass slop emails? So what is it really?

Wes: My emails aren't slop, man.

Simon: And I hope not. But the so the first is clarifying what we actually mean. Let me give you example.

I use this myself and I use this with all our clients. It's October. We have defined the top four activities, including prospecting activities, that will move forward the boat the most.

So everybody picks their top four to do every day. And then we track if we Did them or not day by day, so that we create streaks and or we see the lack of a streak. So we have the strategy, we have picked four things.

It can be call one past client per day. It can be make one introduction to two people that can create magic together because they have complementary offers but the same ideal client, for example. It can be start a new conversation with an ideal client that you never met so far.

So let's say you pick these three activities. Now we've solved the first problem, which is clarifying what the strategy is. We have committed to three things to do every day.

That's already a huge step. It's a small step to define them, but it's a huge difference after you write down because you commit. Now you have clarity and you have it in front of you.

So first step: clarifying what is it actually that you mean when you say prospecting. In my case.

5:17—Four actions instead of a desk full of sticky notes

Wes: Look, I've got things written down, I've got I've got sticky notes. They're all buried on my desk. I keep telling myself, I'm gonna clean my desk, I'm gonna get organized, I'm gonna I'm gonna put it into my AI and it's gonna send me reminders and it's gonna floss my teeth for me, but it doesn't happen.

Simon: That's right. So for people Yes. So for people listening, he just showed like for people listening, he just showed like twelve different pieces of paper with information and post its on those papers. So and that's why the

Wes: Am I broken? That's like five sheets, okay. Don't exaggerate. Don't make me look bad.

Simon: Five sheets, a few post-its, plus AI that's remembering him. Now, this is just one thing. On so the first thing, yeah.

On that, more post-its, more post-its, and then on those post-its, there were like seven, eight things. This is just four and it's in front of me. Four and it's in front of me, and it's just it's the only thing in front of me. So

Wes: Here but here's my pink sticky notes. Here's my yellow stick. I got more, man.

I got more. I got more. Or twelve. Ha.

Simon: The first is to simplify, like make it easy for you. You don't you don't enter, you know, the training session and you have to invent a training first. You do your training plan, you think okay, Tuesday I'm doing gonna do easy and Wednesday I'm gonna do strengths oriented, heavy, and Friday I'm gonna do for an endurance piece.

And then when you go there, you don't have to think anymore, you can just do it. You know you have to do sixty minutes endurance oriented training, you do it. So I pick my four, and then there is a time in my calendar, it's an hour, where I should do prospecting, I hit it, and I move on.

That's the piece of simplification. And before I had this, I had all these possible tasks and they were too much and they weren't clarified.

7:14—When the wheels come off

Wes: What do you do when the wheels come off though? So yesterday I was working on my podcast. Riverside changed their menu.

Took me two hours to do a task that should have been two minutes. I was fit to be tied, man. You know, and stuff comes up.

Like I'm I've been cleaning house on my own stuff, right? I was I mean, I drifted for probably three years. Only thing I did consistently was Jiu-Jitsu.

I just wasn't motivated about work. AI's coming out. I was confused by it.

I just coasted. I let things drift. Now I'm like, all right, I actually I like AI because I understand it and I'm using it properly and teaching people how to use it properly.

But I've been I've always been a product of my own product, right? I experiment on myself first, then I go and teach from experience. So I've used this for months now to clean up my website, clean up my contact list.

Re-engage my list. I'm expanding into ads. I've never run I haven't spent more than a thousand dollars on ads in 20 years.

So I'm starting to do some retargeting, diving into that. But man, it's a lot, right? So I've got my CRM.

I've got my emails coming in. It's connected to my HubSpot. I've got templates that I send out to people, but then it's like, oh yeah, you know, I'm sending out a link to my book.

Well my book It's outdated. I got old URLs. I'm consolidating all my offers.

So I've got URLs I don't use anymore, blah. So I ran the book through AI. Found twenty-seven URLs I needed to update.

So okay, so now stop. You know, there goes two hours, three hours updating that. You know.

So it's like every time, you know, it's like remodeling a house. it's just gonna be Three weeks and you know, ten thousand dollars to redo this room. You pull the floorboards up and there's mold and then busted pipe and six months later, forty thousand dollars later, you're still sleeping in a motel because your house is inhabitable.

9:16—Do the 10%, let Claude Code do the 90%

Simon: Let's stay with that example because everybody's experiencing that right now. You want to do bigger stuff, but then you end up really in fighting fires basically and putting off fires, like the website and the podcast. So with the website example, we can split it into the admin or the tactical part and the strategic, right?

Your strategic part is actually thinking what should I do with the website?

Is it still in right shape? So you are defining what is right shape. And that's the really important 10% of that task.

And you take time to do that. And now the next 90% is really just going through the links, updating the links, deleting some, re-indexing on Google. That part can be done by Claude Code.

So the wise thing for us to do is. What's the ten percent that I do and when do I do them and how can I enable Claude Code to finish it? I have a list of projects.

This would be a project. I would call it website updated. And then I would kick it off.

I would spend a few minutes, probably 10-15 minutes, thinking about what's the ideal website right now. And then I would give it. I open the terminal, I give it to Claude Code, I have it finish and then check off the project.

I look at the final quality. So I put in 10 minutes. Does for the next two hours whatever it needs to do, because it creates subagents, and then after two hours, it sends the report.

So three hours later, when I have time, I check the quality, I say, okay, go. And it publishes the page. But that has now multiple things.

Like we have a list of projects. So I think about, I clarify what matters right now to me. What do I commit to?

What has my attention? What do I really? Wanna put my time in.

And then I do the first part, the strategic, where I decide and I define what done looks like. And I will have either my colleagues, but I have less and less colleagues now that AI is so powerful, to be honest. It's so much easier to spin up an agentic collaborator now and I have 43 of them running and they do exactly this.

We updated our website yesterday. And it took 10 minutes of me, but it took two and a half hours of agents finishing it. And it was just a small update.

So it could easily take three hours if we let that happen. So I start with my top four. The top four need to be boat movers.

12:04—His morning: hot, warm, then cold prospecting

Simon: Of course, later on stuff will explode. That's not in my control, but I expect it to happen. Some fire will start.

Probably one or two fires will start. So I try to control what I can control. It's the early morning.

I start with two hours of a workout, because that's in my control. Then kids, because I have three kids. And then I move to my office, which is a room here in at home.

Like many probably listening, right? And then I start with my top four. And that top four must be needle movers.

So if I do them, they really move the business forward. And it starts with prospecting. It's hot, warm, and cold prospecting.

I start with hot. Who showed me buying interest this last 24 hours? So people who downloaded something from our website, if they downloaded multiple things, I get notified by the agents.

And that's the list of the first three, four people. Usually overnight, three, four people have downloaded heavily. And so the agent scanned them if they fit my ideal client criteria or not.

If they fit, I get their LinkedIn URL and a short briefing. They came from this episode, or they have read the book, then they have downloaded these three things. I checked them, they have so many employees, they are in this industry.

These are their last five posts on LinkedIn. So I assume that's what they need to solve and why they booked something on the calendar or why they downloaded something. So I get briefed about the hot ones.

It's three, four usually. Then the warm ones. Warm means they were past clients or they are possible strategic partners.

And then the cold ones. They don't even know who I am, but I will. Try to get their attention, start a conversation.

Since it's only an hour, sometimes I never get to the cold one, but it's fine. That means I have enough hot conversations to move forward. If I don't have anything hot going on, I will move to cold during the same hour.

14:06—Why he asks hot leads for a mobile number

Wes: So are you reaching people? You know, people seem hard, very hard to contact. Even they I've had people like download a report, you know, and then send it and then the morning like a follow up and they'll mark it a spam.

I'm like, what? You just got my stuff. Why you know, like how are you finding it?

Like how to reach people nowadays? Are they more receptive, less receptive? Are you just DMing them on LinkedIn?

Are you calling 'em, you know, and do they give their email for a free report? Like I don't give my phone number for a free report. So how are you reaching even the hot ones?

Simon: So I ask for their mobile number. If they don't want to give it's fine. We won't start a conversation.

If and that tells us if they're serious or not. Because as you say, hey, I don't give everybody my phone number. I'm really serious if I give anybody a phone number.

So they will bounce back, they will go, and if a week later they come back and now they are ready to give a phone number. Then I know, okay, there they went the next step into informing themselves. And then I know okay, there is some form of interest on their side.

Then the agents check if we are the right people for them, if they are the right people for us. That's another 60% off. And now those that stay, that's the two, three people that I will actually call.

And yes, I will call them and say. Hey Wes, you downloaded the pricing power guide. I'm the Simon that created it, so I'm curious. Was it helpful?

Wes: Do so are they answering or are you like starting off with the text?

Simon: Sometimes they answer directly in WhatsApp. I call them in WhatsApp. If they don't, then I will leave a LinkedIn message.

Wes: Oh okay. That's a little easier. Do you ask for their WhatsApp or do you just know like typically their like my cell phone number is WhatsApp?

So and I get some cold DMs, but I don't usually respond to those. Okay.

Simon: W I ask for WhatsApp. And the reason is simple. If they think, no, I'm not gonna give you my number, they don't know, okay, they don't like me.

And it's fine. But I'm not gonna put my time into a conversation with somebody who doesn't like me, right? And if they if we do exchange numbers, that means there is some liking going on already. And then okay, we have a basis.

Wes: Who doesn't like you?

Simon: Oh a ton of people.

Wes: What? Send me their names. Send me your blocked list. I'm gonna reach out to those people.

Simon: P people hate sales guys. Come on, you're a sales guy, I'm a sales guy. People hate sales guys, they love engineers.

Wes: I'm The Sales Whisperer, man. Everybody loves me. Come on.

Simon: Well, good for you.

Wes: So all right. So I mean the WhatsApp I get. I mean you're in Europe.

I mean I you probably have a very global contact list. Is that safe to say? Or is it weighted more in the US or what?

Simon: It's weighted more in the US and specifically California. Over the last years, Texas has been popping up also, and some Florida. But those are actually Californians moving to Texas.

And then we have in Europe some pockets in Berlin, in Zurich, in Vienna, in Finland. So there are some pockets in Vienna, but mainly it's US.

Wes: And is that just because those are the biggest state? I mean there's more. Those are the three big states. You know, three of the top five probably.

Simon: They're huge. So he and that's why I stopped. So when I started having the first ten clients in California, they started telling the others at barbecues, at events that they go together, hey, call Simon.

Like he helped me with sales processes, call him. And that was enough actually when I realized the size of that market. I and I'm like you, I've never spent any serious amount of dollars in marketing ever.

I do YouTube, I do podcast, I write a book every five years. And that's the inbound part.

18:19—Why he writes a book only every five years

Wes: You have AI. You should write a book every day.

Simon: Well, just because you could doesn't mean that you should do it, right?

Wes: Hey, I'm don't I'm The Sales Whisperer. You take my advice, okay? Then

Simon: You know, the how many books

Wes: But seriously though, mean but why five years? And look I cause I'm kinda changing my own path like literally this week I've been looking at stuff. I was updating my book and I was like, you know, I've got a ton of content that untapped, right? And I'm like

Simon: But when I write a book, I put in my whole soul, my whole life. So three years is just crafting it. One year is refining it.

The first one what was with the publisher. The second one we did on our own, Jay and I. And but we put our soul into it.

So the whole program and the program was hundreds of questions from real participants, from real business owners. And we went back and forth with them. So I really like, you know, I don't think that the world just needs a book.

I think they need condensed experience. Like hundreds of your coachings, that's what I want to read. I don't want to read, you know, three ideas that AI enriched.

I wanna read the experience of Wes over the last five years. That's what I wanna read. 'Cause there is his soul and his relationships in there and his learnings and how he got punched in the face and he stood back up again and now he's back.

That's what I wanna read. And it takes me five years to give birth to such a beast. That's why I did only two so far.

19:57—AI content without the slop

Wes: That's cool. and that's true. I mean there had a guy on yesterday that's a SEO expert and we were talking about AI slop and you know getting dinged, even punished for over producing, you know, and you can't just throw up a thousand blog posts in a day and, you know, think you're just gonna dominate search. So that's good to hear your approach.

Simon: I do one blog per day, so I guess that's prolific, but it's short. It's what I'm just learning right now, or a questions that I got, and I'm answering them.

Wes: I'm torn. Like I've I'm experimenting with my Claude install and we've created some code that kind of supercharges it. But I had it turned on and I've probably got fifty drafts, you know, that AI has written.

'Cause it can produce so much, right? I mean you can't keep up. And I haven't even taken the time to go read what it I've got it on a schedule and it's producing, so I may go back through and read it just to teach some people 'cause like I've got some folks in my Inner Circle, like they're in commercial insurance.

You know, they're not gonna get found without some effort. I mean, it's a boring industry, you know, it's but it's a necessary evil. And so I'm telling them, let AI write a couple blog posts a day for you for a month and kind of front end load it, you know, not a hundred, not a thousand, you know, two a day.

See if you can start to get a little bit indexed. And if nothing else, have write about the critical things that people are interested in your field and have an answer for it. You know, and then because Claude can publish to HubSpot.

And publish to a Google Doc. So then, you know, I said, look, after a month, you're gonna have forty, sixty, seventy blog posts. There's a little booklet you can create.

When you visit a client, you can just drop it off or prospect. You know, it's cheaper than a coffee mug and it's more impressive. You know, 'cause but nobody's gonna read a hundred pages of commercial insurance.

You know, but it's a validator, you know. In the eyes of the prospects. So, I mean, that's one angle, you know, I'm taking for it.

But otherwise, you know, like there's a young guy in the group, you know, and I said, Look, you can have AI write this stuff. That way you're not staring at a blank screen. I said, But you need to go rewrite it.

So you can internalize it. So you understand why you're different. You know, 'cause if you just have AI posting stuff, you're never gonna know the an you're not gonna learn.

Somebody's gonna call you and based on the your content think you're really good and the reality is you're just fake. I guess AI wrote everything. It's a crazy world.

Simon: And that's why I don't lead with AI. I only have AI add like four more arms to people. But it's not it's still the same person.

So it's Simon and this Simon is still doing his thing. He's helping some people. And some of that becomes the next marketing piece because while he is helping, he's learning stuff. And so that learning piece becomes the content of that day.

23:20—One 10-minute video, nine pieces of content

Simon: The only difference is I have six arms now instead of two arms because they can write faster, they can pick it up, they can multiply it. So right now I'm doing one YouTube video per day because it just takes me ten minutes. I record a 10 minutes lesson, and Claude edits it turns it into a blog post, LinkedIn article.

Blog article on multiple blogs that we have, and it turns it into nine things and it schedules it. They go out at the right time in the right order. I mean, that's awesome.

It's 10 minutes of my time. I just record and the rest gets done. We have only one manual step.

We pick the thumbnail because I don't like images that are created by AI. So we craft our thumbnails by hand with the help of AI, but it's us in the mix.

Because I want to express something. It's like a little piece of art. I want to express a specific message and a feeling, and I want to express it in a certain way.

So you see our brand colors and the way we try to communicate, right? So I really think a ton about that thumbnail, and then it goes out. But all the boring stuff, 90% of the work, which is editing, typing, transcribing.

Adapting to a different channel, like on LinkedIn it's it has a different format than on X. So all this boring stuff is done by Claude Code.

24:53—Can AI edit your videos now?

Wes: Do you does your AI is it good enough with video? You know, to edit it, chop it up, distribute it? Cause I've run into some blocks.

It's like it like I'll use Riverside, I use Opus. There's a little bit of an overlap, but you know, they edit a little bit differently, but then posting that to YouTube, embedding that in the blog post. Seem like there's still some manual steps.

Maybe I just haven't haven't dove, dived deep enough into it to automate all of it or most of it.

Simon: You yeah, try it out. It is ready. Meanwhile, it is ready for full production.

So we had the last four months we had only the so called refinery, where I was still a lot the person in the loop. But now a few weeks ago, in our mastermind, Sean, who is a member there, said he's spending two hours editing. And I said, Sean, you're the CEO, you shouldn't spend two hours on editing.

I don't wanna see you spending a single minute on editing. Let's see if AI is ready. To do that.

And so we tried. And then a few hours later, I tagged Sean in the community. We have this real time our own app where we talk back and forth 24/7.

And so I tagged Sean and said, Dude, I got very good news. So Claude can do it can do it really well. Check out my own video.

It's on YouTube since a few minutes. And it was really good. And the y the video was about how to use Claude Code for editing.

And so I put it on The Sales Show on YouTube. I gave him the link. And you know, Monday he asked this question.

On Tuesday it was solved. And now we're giving away the whole workflow to everybody in our community. Because it saves them time.

And we are all about time freedom. The book that Jay and I wrote is called Time Freedom.

Wes: Oh yeah. Are you using Riverside or what are you using to record?

Simon: I record on Ecamm, and the rest is taken over by the refinery agent. He will turn it into articles, blog posts, social media, everything. And meanwhile, they also edit.

So my first 900 episodes, they were all very mediocre because I've never edited them. I ha I'm religiously dedicated to not waste my time on little things. I'm the CEO of the ship.

So I have to look at the big rocks. And I have to move the boat forward. So I'm very careful not to do admin.

So I would delegate it. And now that I can delegate it to AI, now I have it also added. But the first 900 videos were not edited at all.

I had a few tricks like live production with multiple cameras, etc. So it's still it. It's still interesting, even if it's not edited.

And I got away with it because our community was built over many years. So we grew up together. We're growing our businesses together.

So they are nice to me. Even when I do a mediocre video, they go like, Yeah, but I still learned something. he sucks at video, but I still learn something.

Wes: Ah all right. All right. I'm gonna see how little I can touch your episode.

So you're the guinea pig. If you come out like green and with horns, that's your fault, okay? I you forced me to do this.

Simon: Fair enough. That's the cost of being on the frontier of technology.

Wes: 'Cause I'm you know, I'm pretty meticulous and I kinda slowed down what I was doing because it was taking too much time and I didn't want to spend that much time. I took about six months off from doing the podcast. It was my first real break in thirteen years.

It's like I gotta s I gotta streamline this because, you know, promotion is key. You know, just having a podcast, it's not enough. You gotta chop it up.

You gotta s you gotta share it, you know, you gotta get the word out. You know, are you pushing this to like a buffer or something to then distribute it or do you have your agent create like natively formatted, you know, segments and posting directly into X or, you know, Instagram or wherever?

29:08—Inside the refinery: 274 workflows

Simon: Let me tell you the full refinery. So the refinery is one of the two hundred and seventy-four workflows that we have going on. And the refinery means Simon puts in ten minutes.

Wes: You only have two hundred and seventy four workflows. The minimum was two seventy five to be on the podcast, so

Simon: I'm sorry. I will come back next week.

Wes: May have to delete this and you know. Two hundred and seventy four. What the what?

Simon: Well, we're twenty three years in business. So we have processes, right? Whenever we build something for a client, a marketing process, a sales process, and it works, we will share it with the next a hundred clients, right?

As a template. And so that template becomes a workflow as soon as you simplify it and you make it in a way that they can plug it into their world. And so over time, we created all this.

One is the refinery. When I put 10 minutes into recording, that recording gets turned into article, LinkedIn article, blog article. Then social media posts, short form videos, that's a YouTube short, and they upload it immediately.

So I don't even see that anymore. They select three to five shorts if there is juicy stuff. Sometimes they say there was nothing juicy there.

You talked so much. There was not nothing bite-sized. Sorry, Simon.

And but sometimes they file they find up to five juicy bite-sized things that they can cut, and then they will push it immediately to YouTube. I saw them pushing it even to LinkedIn and to X. And it has okay views and clicks.

So the shorts go out immediately, and then around an hour later. One email to our whole list, and that email is a little bit more refined. So the email is really in my language, it has the main points that I convey in the video and why people should watch it.

There is an image of like the actual thumbnail, and you can click it. And that one has to go through nine quality control loops. It's basically skills.

That I've built based on how we work. So for example, if somebody here on the team writes an article and it's their first month, there is a few things that I look at and then I improve them and I ask them to rewrite it in a specific way. Those eight things became eight skills.

They are in a GitHub repo and Claude Code picks them up and runs them. For example, one is called The Seven Critics. So we get a first draft of an article, and it's read by seven people who are grumpy for different reasons.

The first one is grumpy because they have three kids and they're at the grocery store. And now on their mobile phone, they get my email.

31:16—The Seven Critics and nine quality-control loops

Simon: And they go, oh my god, another one of these guys. So I hate these sales guys. I get this kind of emails all the time.

And so the second one is grumpy for a different reason. They got burned by an offer. And so it's seven people who are grumpy, and that skill does two things: deconstruct that email.

Oh my god, that word, fake urgency, salesy word, overused word. Not credible case study. So they demolish and they reconstruct the email.

That's one quality control. The next one is David Ogilvy. How would David Ogilvy, the legendary copywriter, how would he criticize it?

Demolish and rebuild. Then the nine emotions are the nine emotions that really matter in marketing. Things like greed, status, Are they really can we tick off at least seven of them?

Demolition, reconstruction. So it would take me a full day to do this whole thing. But it takes Claude Code like twenty minutes.

Wes: So why run 'em through so many iterations versus having one big brain skill set?

Simon: Then the email is ready, email goes out to our whole list.

Wes: That writes in your voice.

Simon: If it's one, it will still be felt as sloppy because you can't catch enough nuances. We run multiple experiments and the sweet spot, like the minimum quality control loops was eight to nine. So we run eight to nine of those.

And if you don't run it through this, let's say very sensible readers, it's very easy that you piss them off. Because all these emails that they're getting, they're all sound the same. Even the good ones, they're so similar.

And so we are trying to go for this similar. Create a fresh experience. Somebody that's actually talking to you.

34:05—If you do it twice, make it a system

Wes: Cool. You know, I got lucky finding the local guy that's a software developer and he spent months customizing Claude as only a developer could, right? And it's we call it HANK.

And it's got a quality control and it spins up agents as needed and it's got my voice and the skills and so it's very much along the lines of what you're doing. He just structured a little differently. But yeah, I love I've told people forever, you know, I've sold Infusionsoft since 2008.

So it's all about automation, you know, and I tell everybody look at what you do two or three times a day or four or five times a week. If you do it that often, you need to have a process for it, you need to document it, and then you need to automate it if you can. You know, and so AI lets us finally do that.

You know, like with Infusionsoft, HubSpot, you were limited in what you could really automate. You know, with AI it's you're almost unlimited, but people still don't think in terms of processes. It's just not natural. And so they just tolerate it.

Simon: That's the main that's the main message, really. That's the main message, guys. If whatever you do, right?

If you're doing it twice, make it a system, make it a template, make it a checklist. And really whatever you build, and that's why it takes me five years to really craft a book. Because and as you say, I c I could spin out one in ten minutes.

Yes, I could. But what takes me five years is It's only worth really my time if it's not just a solution, but it's a system. So for it a self-contained, repeatable system that everybody can actually start using, implementing, and it will compound for them.

So for example, the first book, Strategy Sprints, it's how you accelerate sales in 90 days. The second and it's a full system. Like each chapter has checklists and the whole workflow on how you do that.

The second book, Time Freedom, it's 13 levers, and you can literally use them. Like, for example, one is licensing. How can you license your knowledge, your models, your thinking, your systems, your methodology in a different country?

Like we have licensing deals with Japan going on with the book, and the book was a Google Doc. So that's one chapter. How you do licensing deals.

And so it takes me five years to come up with the system, then to do it long enough that I know, okay, this really works in different situations, and then in different industries, and in then in different countries. And then people start using it. Now they ask me all these questions.

And when those questions start getting very similar and I have FAQs already, then I know, okay, now the system is kind of ready. Now it's robust. That's when I actually write the book.

Wes: I just found your video here. Stop editing your videos. Claude Code does it in five steps.

But you got another one. Fire well, this is I guess an interview, right? Fired a CRM and hired forty-three AI agents for two hundred bucks.

So I'm gonna go watch that next. How to automate B2B sales with Claude Code. All right.

Simon: That's the one. It's pretty exciting.

Wes: You're firing me up, man. You're firing me up. I'm getting inspired.

Simon: It is exciting, right? I mean we can have six arms. Who doesn't want that? I want that.

37:35—The sales gym model

Wes: I just want longer arms so I can reset spot that itches in the center of my back and I can't get to 'cause I old man's shoulders. So six arms are just two like really long ones. Or like six really long ones.

Or I like six shorts, two long. I don't know, it's kind of a mix and match. That's cool.

So what are you selling? Do you have are you doing one on ones? Do you have a community? Sounds like you got a little bit of both.

Simon: What I have, I have even an image. Maybe people even see the image. I have a so-called sales gym.

So it's like a gym, and your people know exactly what that is, right? You come in, you can have just the key and come in and you use the equipment on your own. So the there is the key for a monthly subscription.

That's our app. They use the 274 tools and workflows, they apply them, and they go in whenever they want, they get out whenever they want.

Wes: Sales gym. Nice.

Simon: They decide their intensity. Now, sometimes you're in the gym.

Wes: Are you letting them like download the MD files and skills? Like do they keep 'em?

Simon: Yeah, they get access to everything. Everything. And then sometimes they are in there and they go, wait a moment, I want that class.

I see those classes, like there is the CrossFit class, the boxing class, you know, the lead gen class, there is the closing class, et cetera, the prospecting class. And they go, Oh my God, I love the energy, I love the music there. These people look cool and they're all fired up.

I want to hang out with these guys. I wanna be, you know, in this energy field. Because when you are doing a 60 minutes class with 15 people, It's much easier to do the exercise and it's more fun.

Because there is the music, there is the trainer, there is just this vibe. And so they also book some classes. It's weekly classes, 60 minutes, very similar to what you would do in a gym.

And then some of them say, Well, but I have 15 people, so I don't want to be in a class. I want us to be the class. Can we just be a closed class?

And that's personal training, basically. And the three things have different pricing points. But everybody can, you know, pick their vehicle that fits them well.

And everything can be tested seven days free. 'Cause how do you know if you really like it, if it's the right one? You can't, right?

So you have to try it on for size. So it's a seven days free trial.

40:02—Why he built his own app

Wes: Are you doing this through school or how are you delivering it?

Simon: The I this is on Kajabi, but it would work everywhere.

Wes: I'm dusting off an old school group. So 'cause I like leading groups. I like doing, you know, your exact model, you know, working with people.

And small grad I had my Inner Circle call just before this. We're doing on Thursdays. And then I have what I call 12 Weeks To Peak™.

So it's you know, private coaching, but sh a short sprint, you know, like not a year, not a week. You know, you takes time to implement and build new habits and so very cool. I like what you're up to.

And then yeah, I haven't used Kajabi in a long time, but they've come a long way. But at the end of the day, I you gotta pick your horse and ride it. You know, I see people switching, juggling, and like find a tool and just use it.

Simon: No platform is perfect. But yeah, when you pick one, just ride it. So the reason I picked Kajabi is I wanted to be on the phone of my people.

To if they say, Okay, I'm gonna commit to this task, I want their phone to remind them and say, Ping, hey, Simon is asking what's the progress? Hey ping, Simon, I'm hanging.

Wes: Yeah, like a mobile app.

Simon: I wanted to do this, but now the terminal doesn't speak to my CRM. Can you help me? So we I wanted this quick back and forth channel when they need it, just for this quick breakthrough when they hang somewhere.

And the best way to do it is an app on a phone, because we always have our phone with us, it can ping us. And that's why I went with Kajabi, because They were at that moment the only ones that had an actual where you can build your personal app as a community host. And I'm glad we did it because the app is really the most immediate way to talk to each other.

Like my really important people, I send them a WhatsApp message or they talk to me in our own app.

Wes: So your own app it that's enticing and interesting 'cause like I've been in WhatsApp groups. Like I've been in one, the guy said he's closing it. You know, it's 'cause it was free.

And so I think there's that. People weren't really using it properly, but it just seems so damn noisy to me. It's hard to track.

So like I've got a group on LinkedIn, fifteen thousand members, but LinkedIn is just not conducive. So I'm gonna try to move people off of there. Onto Skool and just to get better engagement and communication.

So you know, have you found that as well? Like it and you know, and I'm older, I get it. I'm fifty six, but I don't know.

I'm pretty technologically savvy. WhatsApp all those. The WhatsApp, Discord, Telegram, Signal, I mean, they're all the same.

It's just it feels like just this constant stream of noise. And it's like You can't focus, you can't do deep work if you're just getting pinged all the time and there's, you know, seven nested threads under one and you gotta scroll up and where was I? And like, have you found that to be the case?

Simon: Absolutely. Both with our own community and with our clients. So for example, most of our clients and also us, we started with a Facebook group and then you have ten thousand people, forty thousand people in your Facebook group, and then you realize, well, engagement is going down actually.

You have more members, but you don't have more conversations. Because Facebook and Skool is similar. They are incentivized to actually drag the attention of your members away to the next group, to the next group.

Because their business model is, you know, circle them around. What you want is: hey, let's keep focused on this one thing that we are solving. And so Facebook and Skool make it pretty hard.

Then we move on to Discord. It's a little bit better, Discord and Slack. But you still have this similar problem.

And then m our experience was when you have your own app, now you can be on the top screen of a phone. And that's a little bit different. Like on my screen, I have only nine apps.

And so if one of them is where I'm really committed. That has a higher chance to actually get my attention during the day. Together with email and WhatsApp and LinkedIn.

But yeah, these are the decisions that need to be done. And it's not easy to hold the community engaged. And there are a few other strategies like live streams and coming together and challenges.

Like we do 30 days prospecting challenges, we do 60 days closing challenges, all kinds of quests together because you need to gamify it, you need to make it fun. Also, something that I learned from sports, by the way, you need this competition. Like in CrossFit, you always have this leaderboard and you see who is on top and you want to get there.

So I'm a competitive rower. The New Zealander are some of the top rowers on the planet. And it's peculiar because they're just five million people. So how can they win?

44:56—Leaderboards: what New Zealand rowing teaches about sales

Simon: Against the US, against Great Britain, and it's pretty hard. And it turns out they just put their best athletes all into one training center and they gave them an app which had everybody's results every day. And they had two outliers.

Those two they were Winning the Olympic championships, and they were like absolute outliers. Like they were pushing out 800 watts when everybody was doing 660. So they were raising the standard.

And because it was one app, and you would see always, oh my God, I'm just like 15% away from number one. Of course, that would push you. And you see it every day.

You say, Oh, it's 15. it's 14.5. it's 14.2. So you were trying to get there just by having two outliers and one everybody in one app, they raised the standard of their whole country, and it's now a really dangerous team to be up against. And that's what I'm trying to build in Kajabi.

Leaderboard, quests, and transparency of progress and seeing the progress.

Wes: Well That's Well that's the old story of Charles Schwab, you know, in the steel mills. Did you ever hear that? I think it was Carnegie.

I forget who had the steel. I think it was Carnegie. But he had a problem and he hired Charles Schwab to help him raise the productivity and they had like two or three shifts.

I think three shifts. And Schwab, he kinda analyzed things and

He got a piece of chalk and he just wrote a big number on the ground, you know, with on the entryway, you know, whatever. Ten. Like, what?

Like, what was that? You know, it was like the night shift produced ten tons of steel. And then the swing, the you know, the morning shift's like, Well, we can do eleven.

So they boom, you know, eleven. Then the swing shift, what is that? And that fourteen, you know, the boom, boom.

And it just grew and grew just from Having a leaderboard, just tracking, they say if you can measure it, you can improve it. Right.

Simon: And if you can gamify it as a tribe, if you go hunting in sales, prospecting can be very like boring and also solitary. Like I am calling people. It's it's not fun.

But if it's if it's a tribe activity, if you know, okay, my fifteen most trusted entrepreneurs and buddies from all over the world are doing it too. And they will see my numbers and I will see their numbers. And on Friday they will ask me, Simon, how many conversations did you get?

I wanna tell them a nice number. And I'm motivated. Like I wanna be on top of things.

I don't wanna be the only one. Everybody says, Yeah, eight in conversation and I said, one.

Wes: So who's your target audience then? Are these like younger salespeople or are business owners that are still kind of driving sales managers?

48:39—Who Simon serves

Simon: Business owners who are still the main closer. And it's hard for them to get out of it. Because they're the fastest, the best, they have the experience.

And they do not have, like you and I, decades of building sales processes. So they're just good at doing what they do. And that's why they're successful.

And they have five people, 15 people, but they're still. In the weeds of closing. And so there's no deal without them.

So I help them systemize and you know make it independent of people so that they can go to higher leverage activities. I want them to do the 13 things that are in the Time Freedom book. And in order to get there, I need to have them have sales processes that work independently or less dependently from them.

Wes: Because I see that all the time. The owner is very good, but they bring a different skill set and they bring a different energy. You know, and people buy confidence.

And so the owner is more confident. There's just these unspoken, you know, like I say, technique versus talent. You know, the owner has that talent which is not transferable.

You know. You gotta get it out of them, document it and say, Okay, here's the techniques we're gonna teach that become transferable so you can scale 'cause otherwise, I just do it. I just I talk to them and I just I answer their questions and they buy from me.

It's like, well, if your salespeople were that good, they would go start their own company. Why would they need you? You know, they're gonna be different than you.

So getting it out of their heads and getting it going is That's the magic. So if you're making that happen, man, that's why you're growing.

50:21—Raise the floor, not the ceiling

Simon: Repeatable systems. Like that's what I love, that's what I believe in, that's what I use myself. Because systems, they really and you started with saying, Yeah, but stuff happens during the day, right?

And it derails me. Yes, that's what I expect to happen. And when that happens, I don't raise to the level of my goals.

I fall to the levels of my daily habits, of my systems. That's the safety net. That's the minimum that gets done every day.

And I want to raise that floor. I don't care much about ceilings and goals, etc. The older I get, the less I care about goals.

They come, they go. I'm very flexible on the upper side. I really care about the floor, raising that standard, raising that floor so that the minimum we ship each week is a one percent higher.

That's what I care about. Because when stuff gets tough. We fall onto that safety net, onto the levels of our systems.

51:21—A 3-year vision and 70 to 80 projects

Wes: So do you speaking of goals, do you have income goals or is it productivity goals, you know? 'Cause I've always said, you know, closing the sale is a lagging indicator, right? Like losing weight.

You know, I want to lose twenty pounds by January first. I mean that whether or not I hit that goal, it's just a measure of did I do the work for the those ninety days leading up to it. You know, and so if I eat right, exercise, you know, get my ten thousand steps in, blah, you know, stop eating sugar every day, that builds up. So, you know, how do you handle goal setting?

Simon: So I have a personal life vision and business vision. It's in three years. And it says, who are the people that we serve?

Why is it awesome for us to serve them? Which problems do we solve? What's the monetary implication?

So, how much do they pay us to solve those problems? What's the profit margin? What's my net worth in dollars?

And then there is, you know, family and where do we live and how do we live? And my three kids, what are they doing and where do they live and how do they live? And our friends.

So it's more of a it's like a two pages vision. And then I have always projects that work towards realizing that. It's on average, it's 70 to 80 small projects.

That move that forward. And those projects don't really have goals. So it's just right now 70 to 80 projects is what's going on.

And so can be tiny projects like update the website, right? That's a project. And it's done in a day, maybe, or in two weeks.

But I always have 70 to 80 of those things that I select in order to realize the vision, right?

Wes: Did you say seventy or eighty? Or s Okay. How did you keep track of those without technology?

I mean AI's only been a thing for a minute. So five years ago did you have ten projects?

53:25—The Monday strategy meeting and the Friday dashboard

Simon: You know, are you familiar with David Allen, the GTD method? That's a method that I'm using since 23 years. And that's basically natural planning.

So instead of deadlines and goals, rather look at what's here, what has your attention, what do you commit to. And that's what I'm using for my personal productivity, right? As and it's really helpful.

Then as a team. We have two meetings, a Monday strategy meeting. That's in the first book, Strategy Sprints.

How to set up those two meetings. Monday, hey, what's the strategy for this week? this week we want to improve inbound conversion, or this week we want to fill this event. So there is one priority for the week, and then multiple experiments and activities.

And everybody says what's their part. So one says I'm writing the copy, the other one, I'm I'm getting someone on 10 podcasts. Everybody has one priority.

And then on Friday we come together, Claude Code has created a wonderful dashboard, and we see all the activities and the results. So inputs and outputs. We say, hey, Simon has asked five people for a referral, he received two.

We see Michelle has created 281 invitations to the Jetpack workshop to our live event, and we have forty one paid registrants. So that dashboard shows exactly the whole pipeline attention, nurturing, conversions, close rate, follow up that happened, follow up that was missed. And then it says the next opportunities.

Hey, these are the follow ups that you need to do based on deal size and deal probability. And then there is we look at that and try to learn from the week. what do we learn from this? there is less organic traffic on our website. Why?

Let's try to find out. So we schedule a half an hour, we call it a workshop, where we try to find out why is there less organic traffic. But and then another outlier is, oh, but we have more paid members for the monthly event. why?

Okay again, half an hour workshop. Let's find out. Was it a copy?

Was it a person? What's the what's the deviation, both down and up? And we wanna learn from that 'cause what works we will do more of the week later.

55:45—The Investing Show: $50K to $4 million

Wes: Nice. That's amazing. I got everything pulled up here.

StrategySprints.com. I got your YouTube. So you got two YouTube channels.

Why do you do that? 'Cause that seems are you like it's tough to do one thing well, then you chop it up, you know, is it for branding or like why split that up?

Simon: Well, the main one is The Sales Show. That's really the main one. And then from time to time, every couple of years, we run experiments.

So we realize that there are subtopics that catch fire. For example, one subtopic caught fire last year, and then I spun up The Investing Show on the side. Because after, you know, optimizing sales for 20 years, now my clients had money.

We made money. And so The question was how do we keep money? Non none of us had an idea, 'cause we were only good with pipeline Exactly.

And then we had more and more kids. Exactly. And so we had to learn how to actually invest and how to compound money that we have rather than chase the next one.

And that was a skill that we didn't have in our community. And so we started getting smarter. And usually the way I do it is I do it in public.

I start experimenting things. I do it in public. I said, guys, I have fifty thousand dollars.

Can I turn this into four million? This is the plan. Let's find out some strategies.

And so that became The Investing Show. And I'm doing it live, turning 50,000 into four million. We are at 1.4 million right now.

And I'm doing it in public. So we're learning how to have. Ah, when was it?

12 years ago was the actual compounding process, but then making it

Wes: When did you start that? Oh well.

Simon: Public was like three, four years ago.

Wes: But that's cool. Just are you buying like individual stocks? Are you buying index funds? Like what are you doing?

Simon: We have three portfolios with three distinct strategies, and each portfolio has a job. So one portfolio is real estate that's super boring, and the job is just do your five percent and shut up. Then the second

Wes: So you split the fifty thousand across three or as it grew you started to split it?

Simon: Well, the those fifty thousand that was the second portfolio, just stocks. So the second portfolio is Warren Buffett style. Find the most high quality companies and try to keep to hold them forever.

Don't make more than 20 decisions. So really think carefully about

Wes: Twenty decisions, what, a year or twenty companies? Okay.

Simon: In your life, invest in 20 companies because if you are right, then you find five to eight that really compound. So right now in the portfolio we have nine companies. And I share how to evaluate companies and how to find out if a business has longevity, has that edge that can keep them number one.

Or can make them number one in their field. So are they gaining market share or not? How do you analyze that?

That's the second portfolio. That's a stock picking portfolio, nine stocks. And the third portfolio is an income portfolio.

So the job of the second portfolio is to create minimum 12% annualized yield, but we often get surprised by upwards. We got to 14, 16% overall. But 12% is what we aim for.

And it's again, we aim for the minimum because we can kind of control that. We cannot really control the upside. You don't know what happens in the market.

But you know that if earnings are growing, the price will follow earnings over the long term, five plus years. So we look at earnings growth. And then the third portfolio is an income portfolio that should generate 30% annualized.

Because that is selling options and it has two strategies, selling puts and selling put spreads.

Wes: A lot of people don't know what that is. I was a stockbroker when I got out of the Air Force.

Simon: And they should. That's why I started The Investing Show. The I really want people to become financially literate.

Wes: That's good. So all right, so I'm linking there, I got these pulled up. You're a man of many talents.

Simon: I'm a curious person, you know, entrepreneurs are creative people.

Wes: Well it's good though that you can be curious yet still productive. I mean, a lot of people use that as an excuse. They go down rabbit holes and they never launch.

Then they complain about how everything's hard and everybody's out to get 'em and you know, oh woe is me.

Simon: No, yeah, I evolve with my clients. So it's 23 years that I serve only entrepreneurs. So the problem number one that entrepreneurs bring me is lead gen.

How can do I fill pipeline with the right people that can buy big deals? And so that's number one problem to solve. Now, if you solve it long enough, after six, seven, eight years, they have enough excess capital, and now they have two problems.

How to make money and how to keep money. And so that's how the second set of tools and processes was born. But I just I still serve the same people.

J it's just that they have the next set of problems, and because we like to work with each other, we continue.

1:01:12—Where to find Simon

Wes: That's awesome. So where should people go? What's the first thing they should do after listening to this?

Simon: We hang out at StrategySprints.com. This is where you can try out the whole sales gym for free seven days. See if you like the people, the processes, etc. It's StrategySprints.com.

Wes: All right. I will be linking to that online in the show notes. Very cool. So what is it? Is it six PM for you?

Simon: Something like that. it's evening.

Wes: Well, it's not even noon here, so it's really early. Well, this has been awesome. Man, you answered Did I miss anything?

Simon: Thank you, Wes. We covered a lot of ground. I hope we could bring some inspiration to people. Thank you for having me.

Wes: Hey, this has been great. Simon Severino, all the way from Austria. Thanks for coming on the show, man. It's been great.

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