Catalytic Leadership

The Shift That Ends the Founder Bottleneck (Without Burnout)

• Dr. William Attaway • Season 4 • Episode 28

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If scaling your agency feels heavier than it should… if every fix creates two new problems… you may be facing a Founder Bottleneck.

In this episode, I sit down with Simon Severino, the CEO of Strategy Sprints, author of Strategy Sprints, and advisor responsible for $2 billion in additional sales for his clients over 21 years.

We unpack the shift from advisor to CEO, why scaling gets lonely at the top, and the weekly planning system Simon uses to eliminate chaos without adding more effort. He breaks down his Focus Card framework, input vs. output metrics, communal sales strategy, and how a consistent planning process beats chasing the perfect plan.

If you’re building systems, refining team performance, and scaling past 7 figures without burnout, this conversation will sharpen how you operate, Monday to Friday.


Books Mentioned
- Strategy Sprints by Simon Severino


To connect with Simon and explore the Focus Card, sales tools, and Sprint Club community he mentioned, visit strategysprints.com. You can access their tools and even enter their community free for seven days.


Join Dr. William Attaway on the Catalytic Leadership podcast as he shares transformative insights to help high-performance entrepreneurs and agency owners achieve Clear-Minded Focus, Calm Control, and Confidence.

Connect with Dr. William Attaway:

Dr. William Attaway:

I'm excited today to have Simon Severino on the podcast. Simon has created $2 billion in additional sales for his clients over the past 21 years. Simon Severino is the author of Strategy Sprints and the CEO of Strategy Sprints. As an advisor who became CEO, he had to learn the importance of working on the business more than in it. He's a TEDx speaker, a podcast host ranking to the top two and a half percent in the world, a Forbes contributor, and a triathlet. When he's not supercharging sales, you'll find him swimming, biking, running, and tricking his three kids into outdoor activities so they can't escape his annoying, shrinky questions. Simon, I'm so glad you're here. Thanks for being on the show. Thank you, Dr. William, for having me. Hello, everyone.

Intro:

Welcome to Catalytic Leadership, the podcast designed to help leaders intentionally grow and thrive. Here is your host, author, and leadership and executive coach, Dr. William Attaway.

Dr. William Attaway:

I would love to start, Simon, with a little bit of your story. And how did you share that with our listeners? Particularly around your journey and your development as a leader. How did you get started?

Simon Severino:

I started by being utterly confused as a 20-year-old who didn't know what to major in. I had no idea, literally. I went with philosophy because that gave me more time to think about it. And when I came out, the only good thing is I came out with the best grades. And that gave me the opportunity to be in these big advisory houses. Because the strategy advisories, they would look for people who are able to think and problem solve and structure problems independently of their background. And so they took even philosophers. And that's how I started. And I did fall in love with strategy, market strategy. That love has stayed until today. I love, give me a market-related problem. Like, how should how do we solve the pricing? How do we get more people to sign up? Like, give me a big problem. How do we get our sales pipeline full? It's empty. Give me a big market problem. And that's the struggle that I want. I'm here to serve entrepreneurs. That's my personal mission. I'm an entrepreneur myself. And I like big problems. And the big relevant problems that I get asked to are around marketing. And so that's that's what I do now.

Dr. William Attaway:

Love that. Moving from an advisory and to becoming a CEO, that's an interesting trajectory. And not a lot of folks make that turn. What was what were some of the things that you learned during that season?

Simon Severino:

It's a totally different ballgame. When you advise, you think you're smart, and you always wonder, why don't they do that? Why you told them what to do? Why didn't they do it? And now and now you're on the other side and you go, oh my God, this is really hard. It's a hundred moving parts. It's impossible. I saw one thing and two other things break. Yeah. It's impossible. It's like having three kids. I'm a father of three. Forget it. You can't be a perfect father, perfect husband all the time. And so you have to accept that you can't do it and literally ask for help and say, okay, I cannot be the best father, best husband, best CEO, best sales leader. I can't help me. I ask Jesus, but insert your belief in here, ask for help, ask your community, right? And that was the moment that changed it for me, actually. My vulnerability. I can't do this alone. That moment changed everything. Of course, of course, it made me sad, right? It made me feel my own exhaustion and my own weakness. But it's it's there, it's real. And in that moment, but it's temporary. Because in that moment, when we say, I can't do this, I need help, in that moment you realize all the help that's available. We're not alone. And we are in this connective tissue. And for me, I changed working from one-on-one into working more in groups. And now we have even our community, our 24-7 app, the Sprint Club. And so sales and marketing can be very lonely. Oh, I have to do prospecting, I have to do this, I have to call people, I have to write a post. Some people just stop liking it or they really hate it. And I think one point is because it's lonely, because you think you have to do it alone. So I changed a lot of that. I turned sales into a communal activity. I don't have to do this alone. How many people right now run a business as a solopreneur or tinypreneur team and are feeling this? Why don't we get together, guys? And so I started a sprint club and say, I'm struggling with sales. I have to do prospecting every day. I cannot motivate myself every day. Some days I skip it. And I shouldn't. Because it's it's vital. So who feels the same? And people were like, oh, I feel the same. I feel the same. Okay, let's do it together. This is how the sprint club started. And now we're pushing each other, doing challenges, motivating each other. Look, I found this video. Oh, I tried that thing, it works. And now it's a communal thing. And that changes how it feels because now you have meaning, you have communal means also enjoyment because we are social animals as a human being.

Dr. William Attaway:

Simon, so many things you just said resonated with me. You know, as a person of faith, I totally get this understanding and acknowledgement that we can't do everything in our own strength and power. You know, I mean, every morning I you can't see it on the screen, but there's a chair here by the window. And this is where I start my day. Start my day in prayer and in reflection as I'm as I'm reading through scripture. And it's it's a reminder of what I am and who I am and who I'm not. And I need that reminder, you know, because as you say, not only is there more to do than any one human being can do when you're the CEO of a business, but there's also the fact that I don't have all the skill sets and all the gifts to do everything as well as other people can on the team. And learning how to empower them and equip them is key.

Simon Severino:

Love that you bring in this aspect, what I am not.

unknown:

Yes.

Simon Severino:

That is also liberating.

Dr. William Attaway:

Yes. Right? Right? Because you free yourself from that expectation that you have to be world class at every single thing. Yes. Guess what? I'm not. Yes. Yes, and you probably aren't either. Uh no, most things I'm terrible at.

Simon Severino:

And everybody knows it. That's right. That's right. That's right. The list of things that you don't do should be longer, much longer, than the list of things that you do. And so we do this. One of the exercises in the first week of onboarding in the sprint club is you define your ideal client, five levels tape, five things that make your ideal client, and then the five opposites. So that you know, oh, if one of these five things happen, you are not who I'm here to serve, and I am not the best one to serve you. So I will respect your time, not waste your time, and move on. That's so good. You're not my people. And that's a that's a very good exercise ad negativum to say, okay, who's my anti-ideal client profile? So, listeners, do it, do it right now. Stop this. Make a list of five things that make your ideal client, five criteria that make your anti-ideal client, that alone might be helpful today.

Dr. William Attaway:

What a powerful exercise. I love that.

Simon Severino:

Yes. And because we do that in public, we do it in a communal way in the sprint club. So it's our own app. Imagine it's our private Facebook, basically. And it's just us, 246 of us, business owners, small business owners. And so when I do that in public, the other people say, Oh, Simon, you just said you don't do manufacturing, you don't do e-commerce. You know what? I do e-commerce. Can I refer you people? And you refer me the people. And so we start doing what we call power hours, where we make referrals. We make introductions. And I can say, oh, sorry, Paul, I'm not the best one to help you because I don't do e-commerce. I only do high-ticket sales. But here is Laura. She does e-commerce. Can I introduce you? She's also in the Sprint Club. Here's her profile. And now we're starting making introductions for each other. Again, a communal sales activity because it is sales. It is literally sending them a possible client. They're pre-qualified, pre-filtered. There is trust already. So it's a great sales activity, but it doesn't feel weird. You don't have to call strangers and interrupt their day. You're helping somebody.

Dr. William Attaway:

Yes. That's so good. I think the communal aspect of this is key. And I love that you have built a community in the Sprint Club where entrepreneurs can encourage each other, can learn from one another. I mean, we sharpen each other's saws that way. You know, I think that is what is missing in so many leaders' lives. And that's why there's such a prevalence of people feeling alone, of feeling isolated, particularly with remote work, where you're not around people all the time. And that isolation and aloneness only exacerbates the higher you are in an organization, in the CEO role or a business owner.

unknown:

Yes.

Dr. William Attaway:

And that can be, that can be incredibly lonely.

Simon Severino:

Again, you you bring me to a very important point, which is the different strengths that we have. So some of us, they are overthinkers. They think too much about details and they get paralyzed, they don't get started. And other people, they start very quickly, they are a quick starter, but it's never accurate because it's quick. It's always a first draft. That's one example of what happens in the sprint club. I'm a quick draft guy. So I always get, oh guys, I have this idea. I made a quick draft. What do you think? And then there is other people who are more like lawyers or like accountants. You know, they are very accurate. They never start a threat, but they make it better, they enrich it because they find the risks, what's not working, the details that matter. And so the quickstarters, without those detail-oriented people, they would just create a lot of slop. And the detail-oriented people, without that kick and that inspiration, that nudge from the quick starters, they would never ship anything because they keep it all in their head. Waiting for it to be perfect.

Dr. William Attaway:

Yes, which takes a long time. If you ever get there, I wonder can you really create something that is absolutely perfect in every way? And this is where I go back to what Seth Godin says. You know, just ship it. You just have to ship it.

Simon Severino:

Yes, absolutely. So there is value in quick starting. And one of my big frustrations when I was just a strategy advisor without being an owner myself, one of the big frustrations was it felt like I'm flying to a client, I'm helping them, and flying to the next client, I'm helping them. When am I creating something beautiful, something that's gonna last longer than a week? I felt like, you know, a commissioned painter. I go to Tuscany and I paint that king, and then I go to Denmark and I paint that king. But I wanted to feel it didn't feel right for me. I was I had a longing to be more like a sculptor. Like I'm Michelangelo, and you give me one big piece of stone, and every day I go to the same place and I make that a little bit better, and I have enough time so that I can create something beautiful over years. Hmm. I love that. That's so good. And I had nothing like that. And then I said, okay, wait a moment. If I put everything in one place, instead of flying around, I put everything in one place. I don't know what place that is, but what if I put everything in one place? And so that that's what I did. It was a repository at first in Google, and then it became our our own app when it was built. And now it's all in one place. So every day I can come and refine it a little bit, add something, remove something, and it gets better um week by week.

Dr. William Attaway:

That's so good. Yeah, I I I have to ask this. You know, when I write your bio, you you're you're the CEO, right? You have the the abil you've you're a TEDx speaker, you go speak, you're you're a podcast host, you know, top show, you write for Forbes and other places, you're a triathlet, you're a husband, you're a father of three. How do you balance all of that? Like how do you how do you organize your life and your time in such a way that you prioritize what matters most? I don't balance anything.

Simon Severino:

Okay. I don't even try to balance anymore or to manage my time. I follow my mission. And on a practical level, I wake up very early, 5 a.m. So my me time is before my kids wake up, basically, and before the world wakes up. I have already some time for me. And that time is reading, praying, but it's also working out, so taking care of my body and of my energy. And that, and then the day is really in service. So many people ask me, but you do so many things. How do you do it? I say, I don't really know. I just am in the moment. Right now I'm talking to you. I don't need energy. I'm not doing anything. I am being. I don't know if it makes sense, but I don't have to do anything. I'm I'm being and I'm being in service, and it gets pulled. They need this, I'm happy to serve. From every five years, it becomes a book because it it compounds.

Dr. William Attaway:

So you're you're focused on being present in the moment, doing what you're doing and being where you're needed.

Simon Severino:

Yeah, I'm being me. This is who I am, this is what I'm here to do. I'm here to serve entrepreneurs and to open doors for them, to turn on lights via my tools that I have, the 274 tools. So I wake up in the morning if I think about them. How are you guys doing? What do you need today? And then they tell me what they need. And the next thing happens from there.

Dr. William Attaway:

I love that. It's very simple, it's very clear, and you never wonder what I should be doing right now.

Simon Severino:

And then collaborations start to happen. So, for example, the second book, I was burned out after the first book. I didn't want to write another one. Publisher said, let's do another one. I said, No, please, never again a book. Never again. It was so much work. I hated the editing part, so the biggest part of it. I like writing it, but writing is the smallest problem. That's right. And so I said, no, no, let's not do it. And then I was just not doing it. And six months later, our partner Jay Abraham says, Simon, let's do a program together. And I say, Oh yes, Jay, let's do a program. And by the way, while we build the program and deliver the program, let's write down what we're doing and the questions that we get. Let's make that a book. So now I had energy. But again, it was communal. I couldn't do it alone. But because Jay was on it and he is a remarkable thinker, a genius. He's a business genius. I knew with him I can do it. Power of community. I love that.

Dr. William Attaway:

And three, four, five years from now, that same thing's gonna be true. How do you stay on top of your game? How do you level up with the new leadership skills that your team and your clients and your community are gonna need you to have in the years to come?

Simon Severino:

Not on top of anything, William. Anything. My three-year-old daughter, she tells me what to do. Papa, Papa, pick this up. Bring me there. I'm not on top of anything. We do have a plan, but we never follow really the plan. We follow the planning process rather than the plan. Plan changes all the time, but the process is always the same. That's the strategy sprints method, by the way. It's it's on Amazon. The book is called Strategy Sprints. So the process is something that I can trust and that I follow. The plan changes, but the planning process is always the same. So right now, we look at our focus card on Monday, half an hour, we'd look at our focus card, which is our strategy on one page. On that focus card, it says, okay, those are the five things that matter. And each swim lane is end-to-end, one person. So Simon has one thing end-to-end, doesn't need to ask anybody. He runs with it. Michelle has one, Lou has one, everybody has one. Until Friday, everybody does their thing. On Friday, we come back together and we review, we learn from the week. Each swim lane has a number, an input number and an output number. For example, for a sales process, input number, how many invitations to work together did you did you extend? Let's say it's 28. And then the output number is okay, how many won deals? And let's say it's $75,000. So there is an input number and an output number. Because the input number is in our control, the output is not, but both matter. But if you have only one, if you have only the outcome, you will be frustrated all the time because it's not in your control. And then it's meaningless. If you have only the input, you are doing, doing, doing all the time, but you never get the reward. So you need both sides. And that's the process. So on Monday, we'll look at our strategy on one page. It's called the Focus Card. People can download the focus card for free, by the way, at strategysprints.com. It's for free. And then on Friday, we'll learn from that. What did we do? What did we learn about us, about our clients, about our products and services. And this is similar to my practice as a Catholic, by the way. I go to Mess once a week. It's a weekly cycle. And part of it is repenting, which means looking at where I am instead of where I would love to see myself. Good. So I'm here. Okay. And there is no good or bad. There is just I'm here. And okay, what's next? What can I improve? How can I be better in my role? And then we select one thing. Next week, we will do that thing, hopefully 1% better.

Dr. William Attaway:

You know, it makes me think of the power of evaluation. You know, people think that experience makes you better. I don't believe that. I believe evaluated experience makes you better. And every week that's what you're doing, you know, with your team and with your own self when you go to mass. I think this is key to seeing that incremental improvement over time. And it has to be done intentionally. It's not just going to happen. You're not going to wake up one day and the team say, oh, wow, we accomplished everything we wanted to accomplish. We don't know how that happened, but here we are. It takes intentionality, it takes focus. And I love that you are sharing that tool with our listeners. Thank you for that. That's very generous.

Simon Severino:

Yes, we have a ton of tools. I was I was inspired by, you remember when Elon Musk, no, even before Elon Musk, it was nine-inch nails. You remember the band? They gave their album away for free. Yeah. It was a shocker. And it was a good album. And then Elon Musk gave away like the secret sauce to how he builds the cars, like the engine of the car. And that was a shocker again. How can you do that? Like BMW doesn't tell you how they do it. I was inspired because it worked. It worked for Nine Inch Nails, it worked for Elon. And I was like, what if I can come up with the courage to do this? It might be a great marketing tool. And it was the best marketing is answering questions that you get from your people about your services, about the problems that you solve, right? And working in public. So whatever you do, do it in a communal way. Do it so here in Vienna, there is the coffee houses. Right? The traditional coffee houses, they're famous. A few of them have a bakery. And my favorite one has a bakery with a glass wall instead of a brick wall. So you sit in a coffee house, you drink your coffee, drink your tea, and you see them baking, and they see that you are seeing them baking. It's fruitful for everybody. For you it's an experience. And I I'm more inclined to buy that cake if I saw them doing it, if they're happy when they do it and if they're they care about it, then I'm more inclined to buy it because I saw the process, I saw that they enjoy it. And same thing probably for them. It's more enjoyable if you know that somebody cares about the cake. And it's not just you and then it ends there. It doesn't end there. You do it for someone. And if you see that someone who is waiting for the cake, it's a different experience of baking a cake.

Dr. William Attaway:

That's so good. Simon, I could talk to you for another hour. I think there's so much wisdom and insight that you have shared today. And I'm so grateful for you doing that. Thank you. I know our listeners are gonna want to stay connected to you and continue to learn more from you and about what you're doing at Strategy Sprints. What's the best way for them to do that?

Simon Severino:

We hang out at strategysprints.com. And when you land on our site, there are a ton of tools, focus card, other decision making and sales tools and marketing tools that you can download for free. And also, you can enter the whole our whole world for free for seven days and look around and meet the others and try try things out if they fit you for size. And so I invite everybody to check us out, strategiesprints.com, and you can try everything for free for seven days. We'll have that link in the show notes.

Dr. William Attaway:

Thank you for that. Silent, thank you again for being on the show and for being so generous today.

Simon Severino:

Thank you, William, for showing up for your community day in and day out.

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Dr. William Attaway

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