Roland Siebelink — Host (00:00)
I've already seen the movie. I can predict what the next scene is. And that of course is supremely valuable to all these founders that almost invariably go through this for the first and only times in their lives.

Welcome, everyone. This is a very special episode this week of Breakthrough AI Operators because it's going to be a reverse episode. I am very scared and anxious already because I've had my great friend Payandeh Ekrami, who is herself a very seasoned sales executive in tech enterprise sales. I've had her, persuasive as she is, persuade me to interview me for my own podcast. How scary is that?

Payandeh, welcome to the show.

Payandeh (01:12)
Thank you for having me and for taking the challenge on. It's so exciting to be talking to you and I'm looking forward to doing this with you.

A little bit of background for anybody that is listening and watching — Roland and I were talking and he was sharing with me what it is that they do. And I started asking questions about his background and how he has arrived here, and I was very surprised to learn that he has been at three startups that became unicorns back to back. And he got to see that entire journey from beginning to unicorn state. And that's unique. There are not that many people I've crossed paths with that have had that experience over and over again. I thought that we had to do a session where he shared with us what his story is, why he's doing what he's doing today, and get a good understanding of what he is doing in this world.

Tell the audience about your journey before you went into this accelerator model that you are running.

Roland Siebelink — Host (02:16)
Well I've been very lucky, as you mentioned, to have been part of three unicorns in my younger career, back to back. Every time, we grew a company from some ten to some thousand employees, from one million to a hundred million dollars in revenue in just three, four years time, every time.

I've seen that journey a few times where a company is in absolutely fast forward mode where they may have seven CEOs in those three years. They may have five fundamentally different strategies. Of course, the organization chart changes a hundred times, and it's a fundamentally different way of operating a business than what people will have learned in other jobs or may have learned in business school at some point in time. I started realizing this is a completely different practice.


And it's also different from the early stage startup practice where we've had a lot more thought leadership in the last 15 years, especially coming out of Silicon Valley and out of all these early-stage accelerators. People all have gone through that when they sit on, let's say, this rocket ship, but what they fail to realize is that when you move into that scaling mode, in that acceleration mode, some habits you have to start dropping, you have to start learning new things. And still they are different things from how to manage an established corporation. And so, it was that middle stage where we started to call it the adolescence of a unicorn. It's not a little kid anymore, but it's also not quite a fully fledged adult yet in a boring suit or something. How do we make that phase in particular successful? And that's what I've been passionate about.

I've been through it three times myself inside the company, not just as an investor, as many others have. I've seen it from the front lines. And now I can often tell the founder what is going to happen. I've already seen the movie. I can predict what the next scene is. And that of course is supremely valuable to all these founders that almost invariably go through this for the first and only times in their lives.

Payandeh (04:18)
Very clearly share with us what do you do with all of that knowledge and expertise and knowledge from within an organization, which is a unique thing to offer the world. What are you doing with that day to day as part of your working life?

Roland Siebelink — Host (04:29)
Yeah, so our mission is really to share that knowledge with as broad an audience of mid-stage founders as possible. Everyone who's either going through it now or will be soon, we want to make sure they're aware of this is a different way of managing a company. There are best practices and we want to teach them to people.

Now, of course, we cannot work personally with everyone. A lot of what we do is basically public education, things like this podcast, but I also do lots of speaking events. We do public workshops and other things that are really accessible to a large number of founders, even if they're still a little bit cash-strapped in the beginning. And then for some founders who want more, want custom advice, of course, if there's a really good fit and, like you said, there's a feeling of a deep relation that we can actually build up, then we can do some custom programs where we go deeper into workshops with their executive team on a private basis, some one-on-one coaching, but that's pretty selective.

Payandeh (05:31)
What made you decide instead of repeating that over and over again or becoming a C-suite executive, just developing your career down that path, what made you decide to step out and outside of that flow and do what you're doing today with Midstage Accelerator?

Roland Siebelink — Host (05:50)
Yeah, that's a really good question, Payandeh. And I think it really ties back to what you said before. I don't actually like referring to myself as a coach too much. I like to call myself an accelerator because it's all about the outcome that you try to help bring about for people. And I think with many of these other professions that I respect, of course — coaching, mentoring, consulting — it all feels like you're a little bit on the sideline and you're giving some advice, but in the end, you're not really taking responsibility for the outcome.

One of the best compliments that we got from a currently active client is these guys are not just on the sidelines, they're on the field with us. They care about the outcome. And I think that's really driven me for a long time. I remember my very first job out of college was to actually be a junior lecturer and assistant at the university where I had graduated. And the reason why I didn't stay was because I couldn't stand writing all these studies that would just disappear down a drawer in those days. They were all on paper still in those days, of course, and I couldn't stand not having an impact. I like to have an impact and I like to really make sure that people get into a more successful place in life.

I cannot tell you how many times Doug, my co-founder, or I have to literally bite our tongues and try not to tell people what we think we would be doing, right? But I think it's all the experience — yes, ten years now as an independent company, but then before some twenty-five years of actually doing that inside these companies, right?

I was lucky enough in all these three unicorns to somehow get very close to the CEO and even in my twenties already being like an advisor to them. So I've done it for many, many years. And over the years you just learn that the most effective way for people to learn or to change themselves is literally for them to arrive at a conclusion by themselves and not to be told what to do.

One of the funniest things in our workshop that's literally like a standard operating practice for us is we will always tell a new founder/CEO we work with, when we do the first workshop: can you please make an effort to sit back, relax, and be the last one to speak at any discussion? Can you imagine how hard that is for these — well mostly guys, there are some girls of course — but how hard that is to finally shut up and listen.

Here's what happens. The first hour of the workshop, they're super anxious, 'cause they're just not used to it, right? But they're making an effort and then you see them start visibly relaxing. Like, actually the point I wanted to make, Johnny is already making. Or the point I wanted to really stress, Deborah made before I even did, and she can say it much better than I did. So they finally start seeing that actually a lot of the thinking of the team is already there, sometimes better than they would have been able to voice it.

And then what happens by the time we're ready to break for lunch is that they start seeing that some people they thought were their best talents are really not saying that much and are not contributing that impressively, whereas others that they thought of as the first person to get rid of from the team are actually the best contributor of all. What do you think's happening there?

Payandeh (10:02)
Wow. Some people have original ideas and some people are echoers and that becomes super obvious.

Roland Siebelink — Host (10:07)
Exactly. They start realizing that person I love so much has actually been echoing me all the time and has been very good at always making me feel right. But that's not necessarily what a team needs at that stage anymore, right?

(10:59 — via Payandeh's question)
That's a very good question. I think one early breakthrough moment has to be that yes, you can be passionate about your product and you can be passionate about your company, but you can start separating that from being passionate about every single detail. Because as long as you're still completely passionate about every single detail in the business, of course you're not going to be able to delegate. Once people start feeling like I'm so in the weeds, I cannot focus on the things I should be focusing on — that's the real job of the CEO at that stage. Move from managing by assignment to managing by area.

Roland Siebelink — Host (12:52)
I think just having more clarity between the team members that is explicit — and that typically means on paper or on screen as opposed to just in a discussion — is one of the first steps. People completely overestimate how aligned a team really is. And one of the exercises we often do in the first workshop is ask everyone to write down what they think they're responsible for.

I've seen teams start crying out of frustration seeing how misaligned they found out that they were — for example, the head of engineering thinks they are responsible for never having an outage, whereas the CEO thinks the head of engineering is responsible for launching ten innovations every month.

Roland Siebelink — Host (14:19)
Before I sign any deal with any customer, I will always ask the founder/CEO one very difficult question. Do I work for you or do I work for the company?

It will typically take them about a minute to answer that. And fortunately about ninety percent arrive at what I think is the right answer where they say, actually you work for the company. And then here's a question I learned from one of my own mentors: so if ever I would feel, Mr. Founder, that you're no longer the right person to be leading this company, would you want me to tell you?

Payandeh (15:34)
Yeah, and it also tells you whether he works for the company or for himself — or she, right? What is the ultimate purpose here? If you are humble enough and brave enough to hear difficult news and then figure out how to turn it around or step aside, that's a completely different thing versus no, I don't want to — like this is about me. This is my legacy. I'm legacy building as opposed to business building.

Roland Siebelink — Host (16:00)
One of the best examples was when I was young in the 90s, there was a company in Europe called Orange Communications. They split the entire business between just two divisions — Orange Today and Orange Tomorrow. Orange Today was all the people who worked in call centers, nine to five, sales associates in the shops — all relatively process driven. Orange Tomorrow was kind of like the innovation division where they would hire the hotshots, who would never work nine to five, would come in maybe at noon but then would work past midnight, all on these innovative projects.

One thing that's helped a lot is when we talk about the flywheel of the business. Every business has only four major functions: it's to innovate, to bring something exciting to the market, then to sell it, then to deliver it, and then there's back office which is dealing with finance and people. That's it. And if you think of these as one feeds the other — the innovation feeds the sales and the sales feeds the delivery and the delivery feeds the cash flow — that's how you start seeing that whole business develop.

Roland Siebelink — Host (25:04)
The things I look for in particular — one is, is there a major outcome that they have in mind? Call it the ambition, if you will. And then second, it's this kind of rare combination between on the one hand being very stubborn about their vision and on the other hand being super pragmatic on how to get there. Are they coachable? And ultimately I think it's almost always necessary to see some eagerness for learning in general, especially learning about management and leadership and just wanting to be doing better and starting to see that as a craft in itself.

Roland Siebelink — Host (27:41)
I sincerely believe that everyone can shine in a certain path in life, a certain occupation. Everyone can be excellent. I am not a believer in there's great people and there's bad people. I think it's just a question of fit. And so unfortunately, the tragedy is that the large majority of people never really find a good fit to their talents, never reach the level of self-awareness where they can even assess whether they could get a better fit. And I love helping people basically find a better fit.

Payandeh (29:46)
Well, Roland, I want to thank you for being courageous and vulnerable and letting me join this conversation and turn the tables. It's been such a pleasure talking to you and hopefully the audience finds a lot of great nuggets in the discussion that we've had today.

Roland Siebelink — Host (30:06)
Thank you so much, Payandeh. This was a true pleasure and thank you for taking the initiative to turn the tables on me once. I hope that people learn a lot about what it's like to run a mid stage company in this era of breakthrough AI and that they keep listening.

Payandeh (30:25)
Amazing. Goodbye, everyone.