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IAM1972 – Coach Shares the Secrets to Scaling Your Business

Podcast Interview with Roland Siebelink

In this episode we have, Roland Siebelink, who is a three-time tech founder who helps founders navigate the challenges of scaling their businesses.

He shares insights on the mid-stage of a startup and the importance of being a “clockmaker” as a CEO.

Roland's books and coaching services offer valuable insights and tools to help founders navigate the mid-stage successfully. His books act as a gateway to understanding the challenges inherent in scaling a business and provide exercises to assist founders in helping themselves and their teams.

Scaling a business is a complex endeavor, but with the guidance of experts like Roland Siebelink, founders and CEOs can overcome the challenges and achieve long-term success. By embracing change, adopting a mid-stage mindset, and empowering their teams, CEOs can chart a clear path to product-market dominance. Roland's insights and strategies serve as a valuable resource for founders looking to level up their businesses.

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Full Interview:


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Roland Siebelink Teaser 00:00

My passion here is to help those founders stay in charge for as long as they like. But of course the quick pro quote is companies changing fast, so you have to change along with it.

If you can't change, then it's only natural to expect your investors to want to replace them with a close friend at some point in time.

Intro 00:18

Are you ready to hear business stories and learn effective ways to build relationships, generate sales, and level up your business from awesome CEOs, entrepreneurs, and founders without listening to a long, long, long interview?

If so, you've come to the right place. Gresh values your time and is ready to share with you the valuable info you're in search of.

This is the I AM CEO podcast.

Gresham Harkless 00:45

Hello. Hello. Hello. This is Gresh from the I AM CEO podcast, and I have a very special guest on the show today. I have Roland Siebelink.

Roland, excited to have you on the show.

Roland Siebelink 00:53

I'm so excited to be here. Thank you for the invitation, Gresh.

Gresham Harkless 00:56

Yes. You're doing all the awesome things. The easy thing I get to do is just to talk about Roland and ask him some really hard-hitting questions. But of course, before we jump into that interview, I want to read a little bit more about Roland so you can hear about some of those awesome things.

Roland is a three-time tech founder with a profound understanding of the challenges inherent in scaling a business. Recognizing that this journey can be arduous and complex, Roland is dedicated to helping founders get through it in one piece. Focused on guiding burgeoning startups, Roland specializes in propelling them from the product market fit to product market dominance. He recognized that this transformation demands increased planning, innovation, unwavering effort, and steadfast commitment.

With a track record of elevating three companies to unicorn status, Roland's mission encompasses the transformation of creators into leaders of thriving enterprises. His expertise not only is in crafting exceptionally performant leadership teams, but also in nurturing individuals to become architects of exceptional companies. Roland is like a Jedi when it comes to the startup space. I almost want to call him the Michael Jordan of the startup space because he's had a three feat and he's done so many phenomenal things.

He's just a wealth of knowledge and information's numerous books as well, too. And if I heard correctly, I think you know how to speak at least four languages. Is that right? I heard that on the interview.

Roland Siebelink 02:11

Yeah, I can do business in four. There are a few more I can dabble in, but yes, thank you.

Gresham Harkless 02:16

Okay. That's why I knew you could get the square root of pie question with no problem. So Roland, are you ready to speak to the I AM CEO community?

Roland Siebelink 02:23

Yeah, of course. I'm delighted.

[restrict paid=”true”]

Gresham Harkless 02:25

Yes. Let's get it started then. So to kick everything off, what I wanted to do is rewind the clock a little bit, and hear a little bit more on how you got started, what I call your CEO story.

Roland Siebelink 02:33

Yeah, absolutely. So, at the moment I'm running mostly coaching and facilitation company for those fast-growing startups, working with people all around the world, software, hardware, any other tech business. But the reason I got into that was really that I was lucky enough to be part of three unicorn stories, as you mentioned in the introduction. Every time joining a company when it was around ten people at the outset, and then helping them to grow it to about a thousand people in typically just three years.

So talk about exponential growth, right? These are really huge growth stories. What I noticed is that almost nobody in those companies has actually ever done that before, or even been close to it. So I do think it's quite a unique trajectory that I've been able to see that from the inside three times in a row, from different kinds of functions, whether I was in products or marketing or operations. I've even done customer success strategy, even some finance at some point in time.

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So I do think I'm a generalist, but the red thread was that I was almost always able to build like a relationship with the founder, CEO get into some kind of coaching role with them whether it was as an assistant or later on as a more like peer coach. I really noticed like one, how lonely that position can be and how much under pressure these folks are. But also how they don't actually know the roadmap of what is going to be happening. What are all the caveats they have to watch out for? What are the things to really focus on right now?

Because I've seen that movie a few times, and I can see the company grow ahead of the curve, let's say, I really think we can now add value to those CEOs in helping them understand beware of this, be careful of that. Because this mid-stage that I focus on, it's really tricky. Many founders think that as soon as you've raised your first money or you've got some degree of product market fit, then you're all good to go.

But the failure rate is still astonishing. And a lot of people don't even realize that.

Gresham Harkless 04:33

Yeah, absolutely. And I was listening to one of your interviews. I think you said it's still upwards in the 90 percentile, right?

Roland Siebelink 04:39

Yeah. So out of the companies that get funded the first time, so external funding, we're not talking friends and family and fools, but we're talking actual professional investors like seed investors, right? So out of those actually only 2%, believe it or not, make it to a full exit or unicorn status. That is surprisingly low, especially if you know that, maybe only one out of 100 companies makes it to that funding in the first stage, right? So already I can understand that at that stage, that really feels like a big accomplishment.

It's a 99% chance that you don't reach that, but it doesn't mean your journey is finished. That's where I help people to really get to that next stage. It's like winning your stick with the sports analogy. Although if you looked at my body, I'm not sure you would still apply that. But sticking to that sports analogy, it's a little bit like winning regionals. Thinking Okay, now I'm there. No, when you win regionals, that's only the journey, right?

Gresham Harkless 05:39

Yeah, absolutely. The same goes with a new level, new devil. So like when you reach that level, there's more to definitely be done.

Roland Siebelink 05:46

You have to be on top of the experience. You have to understand exactly what customers are going through, have to take the customer calls. I could go on for an hour, but you get the drift, right? You have to really be on top of all the details.

Now, if you are two, three years later, running a company of 100, 150, maybe even 1, 000 people, and you're still trying to stay on top of all the details, and you're not letting people manage on your behalf, then the company is going to implode, right?

Gresham Harkless 06:12

So could you drill down a little bit more? I know we touched on a little bit on how you're helping your clients, how you're serving them. I would love to hear more about your books and all the awesome things you've been able to share there.

Roland Siebelink 06:21

Yeah, absolutely. So, the books just to start with that's really as a way to introduce people to this way of thinking and to some of the patterns we see and the exercises, if you will, that they can do because a lot of founders, first and foremost, want to help themselves, right? So, this is in a sense, almost like the DIY which almost is our preferred option too. If founders can help themselves and their teams, then why not? This helps us reach quite a bit of scale in reaching thousands of founders with this insight. But for those that need more help or want to move faster or want more momentum we offer typically coaching and facilitation services.

We almost always do that in a package. So we're not just focusing on talking to the CEO, putting them down on a couch and saying, talk to me about your problems. We really think like the way that a company gets to run better is because we both talk to the CEO one-on-one and talk to the whole founding team, typically on a quarterly basis. So what we do in those sessions is really create momentum by doing the quarterly planning with them. They're supposed to do it anyway, so there's no time lost, right? We help understand like what went wrong, but also what went right in the last quarter. Even putting that on the table openly is already a challenge for many teams, right?

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Be able to get to this common understanding, but also openly discussing what are we good at? What are we not so good at? What can we fix and what should be the priorities for the next quarter? And so the goal there is in just one day to align the entire team around, okay, here are the top five priorities for everyone in the company. We know exactly who owns what, we know how it's defined, we know what we need to do to reach those. So as soon as you get out of that workshop and maybe the dinner afterwards, the next morning you're ready to hit the ground running with your teams and really reach those goals and smash them.

Gresham Harkless 08:16

Nice. I absolutely love that process of it. What would you consider to be what I like to call your secret sauce? I feel like you touched on this. It might be that three feat that we touched on and talked about, but what do you feel is the thing that makes you or your organization or a combination of both unique?

Roland Siebelink 08:32

I think it's really the understanding of the specific way of operating a mid-stage business, which is really different from an early-stage startup. But it's also very different from a late-stage startup, let alone an incumbent company. And so what we often see is that a startup grows and then they say, okay, we need to get better. We need to get more robust. Then they start hiring these executives from large companies and they think that they are going to bring in all the best business practices, but they don't realize that what you need at the mid-stage is a very specific way of operating that is neither here nor there.

I always make the analogy with somebody in adolescence. If they still operated like a kid, nobody's going to be impressed that they can talk and they can walk and they can sit still, that's not what an adolescent is successful with. But at the same time nobody's going to be impressed if they behave like a 50-year-old guy in a suit. That is never going to change anything. That's just coasting. Essentially they need to explore. They need to come up with new ideas. They need to sometimes try out things and drop them again.

So it's those same awkward years that we all experience in ourselves and our kids in adolescence, but also as a company. Learning to stand on your own feet, figuring out what works, figuring out what doesn't work, having that combination off agility off, like being able to drop something and try something new, but at the same time, sticking with what works and not dropping everything out of the window in a tantrum every two weeks and saying, okay, here's another squirrel to follow.

That's the secret sauce. It's that mid-stage specific way of operating that nobody really learns either in an early-stage startup or in a mature company, such as Google or Salesforce.

Gresham Harkless 10:13

Yeah, that makes so much sense. I wanted to switch gears a little bit and ask you for what I call a CEO hack. So this could be like an app, a book or a habit that you have or something from your book. But what's something that you feel like makes you more effective and efficient?

Roland Siebelink 10:27

So both for me and for the CEOs I coach, I think the most important hack is, can you manage just by asking questions? And so, especially for early-stage startup CEOs that are moving into the mid-stage that have the habit of like always guiding this and that and giving instructions all around, I tell them like, can you manage just by asking questions? That is a huge hack for them and also very hard for them to implement. But moving from I want you to do this to a question like, what would you do? Or what do you think your goal is? Or what do you think the company needs most at this stage?

One, it generates far bigger insights than they ever held possible because their whole understanding has been like, I am the brains and the other people are the hands and the feet. So, they actually are often surprised how much insight comes out off those people that you've hired, that you're proud of working with and that builds the confidence to delegate more. The other thing is also by only asking questions, you build your own sense of curiosity, and you build this learning muscle that is far better activated in terms of understanding what everyone needs and sees, and how their perspective is different, rather than you just thinking it all through and then giving instructions to folks.

Gresham Harkless 11:45

Yeah, that makes so much sense to me. What would you consider to be what I like to call a CEO nugget, a little bit more word of wisdom or piece of advice, or something you might tell your younger business self, if you were to hop into a time machine?

Roland Siebelink 11:57

I like the analogy of the clockmaker instead of the time teller. I think it came from Peter Drucker or maybe from Jim Collins originally. But in the beginning you were a time teller, right? That's fine. But how quickly can you move to being more of a clockmaker? What I mean, and obviously I mean like the old-fashioned wind up clock that half of the audience of this podcast may have never seen in their lives, but hey, go to a museum and you may see one, right? So I realized that, here, what we're looking for is rather than getting an organization that does exactly what you want them to do every time, how long can this organization keep running by itself and staying on course without you intervening?

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I often in a very early conversation, I'll ask CEOs, like, how long can the organization stay on course without you intervening? And you know what they often say? 30 minutes, 40 minutes, and I'm like what would change in your lives and in the effectiveness of the organization, if we could bring that up to just a day? if you only had to intervene once a day, and it's huge, I could spend so much time on meeting clients, meeting partners, basically doing business development work if I could just rely on things running inside the company.

Then we say typically, it's after a quarter you get to about one time a day intervention, maybe after half a year, three quarters of a year, you get to maybe once every two days, every three days and in a year or so, you'll probably go to less than once a week and you know what that does? That means you can take a holiday, which is probably what the organization needs most at some point in time, right?

Gresham Harkless 13:42

Absolutely. So Roland, now I want to ask you my absolute favorite question, which is the definition of what it means to be a CEO. We're hoping to have different quote and quote CEOs on the show.

So Roland, what does being a CEO mean to you?

Roland Siebelink 13:52]

To me, CEO means guiding the organization, the big picture, not the small picture and the parts of that are like the choices you make in your strategy. The culture you set for the people you want to work with, the priorities you set in resource allocation, and I think that's really it.

Gresham Harkless 14:14

Yeah, that makes so much sense. I think that as we've talked about, you start to empower your team. It allows you to focus more and spend more time, energy, resources, whatever it is on those kinds of essential things that will drive the organization forward. So I definitely love and appreciate that definition.

Roland Siebelink 14:30

And if I may add one more thing, that also means that your job as a CEO is to cover off every single area of the business where that's day-to-day work. I don't care if there's some guidance already, you're responsible for this area. All that stuff comes to your desk. It doesn't come to mine right now. I'll coach you on it if you want me to, but I'll still be off the field and you're on the field. So don't just let it set the organization up so that every exception comes to your desk.

You should set up your team so that every possible area in the day-to-day running of the business is already covered and there's always somebody else in charge first. That's how you become an effective CEO.

Gresham Harkless 15:11

Nice. I absolutely love that. So Roland, truly appreciate that definition, of course I appreciate your time even more. What I wanted to do now was pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know. And of course, how best people can get ahold of you, get a copy of your books and find out about all the awesome things that you're working on.

Roland Siebelink 15:29

Yeah, absolutely. We've actually collected a lot of the resources that we share with folks on one page, which is

So just go to that link, and you'll find links to my books, to all of our online tools that we have, as well as contact information if you just want to be in touch.

Gresham Harkless 15:52

Awesome. Thank you so much again, rolling to make it even easier. We'll have the links and information in the show notes as well, too. I appreciate you for your time, appreciate you for obviously doing all the awesome things you do to make that happen. And I hope you have a phenomenal rest of the day.

Outro 16:05

Thank you for listening to the I AM CEO podcast powered by CB Nation and Blue 16 Media. Tune in next time and visit us at I AM CEO is not just a phrase. It's a community.

Want to level up your business even more? Read blogs, listen to podcasts, and watch videos at Also, check out our I AM CEO Facebook group. This has been the I AM CEO podcast with Gresham Harkless Jr. Thank you for listening.


Dave Bonachita - CBNation Writer

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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