Martin Stellar

Ethical business and curious living

Martin Stellar

Martin Stellar is a coach and consultant for ethical sales and business growth, as well as a former monk, tailor, and copywriter.

Martin has lived an incredibly rich life, with many creative and introspective adventures. He draws on his experiences and years of study in psychology and business, to provide guidance for professionals and entrepreneurs.

I met Martin earlier this year as I took up his offer on a coaching call, curious to see how his experience and framework would apply to this project, Design Disciplin. He gave me food for thought on the ethics and psychology of entrepreneurship that was far more useful and wider-ranging than I expected. In this conversation, we revisit some of those ideas, find some new ones, and dig into Martin's extraordinary story. We discuss mental models that have value reaching far beyond sales and business – we arrive at frameworks we can use to align our professional and personal lives.

The transcript below has been edited for clarity, brevity, and readability.


I met you before for a short coaching session, and I left that conversation with a lot of new thoughts. We worked through interesting analyses and found some interesting directions. But most importantly, the experience itself was instructive.

I've read books and seen presentations that talk about the things we discussed, but the experience of talking to you was very compelling – the words you choose, the way you appear and speak... So if we compare talking to you and reading a book – assuming, for the argument's sake, that the content and benefit is exactly the same – I would actually prefer the experience of talking to you. How do you design and develop a convincing presence and conversational experience like this?

It's a natural form of design, I would say. It's not so intentional, it's not a designed thing. It's simply the compound of years of learning, and practicing, and pulling everything together that I gathered over the years.

The first thing is that, for 25 or 30 years, I've been a student of psychology. It's always been fascinating to me: to learn about people, figure out why people do the things they do.

The second thing that gets added in is listening: really paying attention to somebody. Not just what they're saying. but also to what they're not saying; their micro expressions, body language, what I can piece together from what they've told me about their history.

It's an intuitive process of trying to really grasp what the other person is about, what they're dealing with, what they're up against, and what life is like for them. It's my favorite question: What is it like to be them?

To really try and be as present as I can possibly be, in the moment, with a person; and bring everything that I have to the table, to make this as much of a valuable and memorable experience as I can... That's how I "design" my way of talking, of being with people.

Are there any particular topics, people, or resources in psychology that really drive this?

I've read a lot, in all kinds of different fields. But the way I see things, I would say, is based on Jungian psychology. And there is an an author and coach – "the shrink for entrepreneurs" – Peter Shallard... He has written a lot of articles. I've listened to an enormous amount of webinars with him, and he's really been a very big influence in terms of the psychology of communication; but also on how to show up as an entrepreneur, as a professional. Related to marketing and sales conversations, he's one of my big inspirations.

These days you concentrate on "helping nice people sell," with this idea you call "ethical sales." What does all of this mean? Like, what is a "nice person?"

It's about how you show up in life; to business, and to other people. Why are you in business? What's your purpose? To what end do you risk complete, abject failure by trying to run a business? Is it because you just want to make a lot of money? Or is it because you have something that can make positive change, and you're willing to bring that to people at the cost of potential failure? If that is the way you show up, you have a really powerful motivator. People like that, typically, are people who really care about values, integrity, and doing right by people... You can label that "nice people."

Good people typically struggle very much in trying to get their work in the hands of other people, because we don't want to violate our values. We have our moral ethical compass, so we don't want to bother people. We don't want to make cold calls, we don't want to have a sales conversation, we don't want to do any selling; because we just want to help and serve.

This is very much how I started. When I started as an entrepreneur, I didn't want to have anything to do with sales. The quality of my work was so good, people should just choose that, because of its quality. I would write blog articles, and participate in forums, and that was it. I didn't want to do any business activities. This caused me to fail at my first company. It was a bankruptcy, because I refused to get over myself – my values were so important to me that I wouldn't do anything to actually help people get to the work that I do.

So "ethical selling" is a way of communicating with people that is based on service. It is based on empathy and integrity, with the goal of helping somebody make a decision. And that's the job of the ethical seller: to facilitate the decision-making process; where it can turn out to be a "yes," and it can turn out to be a "no."

If you really care about the other person, their outcome, and their well-being; then you should be OK with "yes" or "no." And that's where the nice people actually have an edge over other people. When we have a sales conversation where I actually recognize that it's not the right time, or not the right product for you; and I direct you to choosing the "no," or I help you discover that "actually, no Martin – at this point with you, it's not something that we should be starting..." Then I serve you in terms of what is best for you. Not my sale, my revenue – I want what is best for you.

When that happens, and when I can take a "no" and say, "that is awesome, thank you, I'm glad you realized this and made this decision..." Then the effect is that you won't remember it as something where you've been pressured or manipulated. You'll remember it as a helpful conversation, as a process that brought you clarity and insight; and where you, in full autonomy, made the decision to say "no." If then, a few weeks later, I come back and say, "hey, how's it going?" – if I follow up, check in, whatever next step there is – you will be much more welcoming, much more open; because you were treated with respect. You felt good talking to me, and you left the conversation with a feeling of "yeah, I'll talk to you again!"

Then, selling becomes something very natural. It becomes a trust-based, friendship-based process of discovery, of generating insight and clarity. It puts you in control, makes you the authority in the entire process. I'm here to have a leadership role, to steward over the quality of the conversation, but in the end, you are the boss – you make the decision.

These are the kinds of things that we talk about in design – like human-centered design or design thinking – based very much on understanding the other person, understanding the customer; and figuring out the product decisions to serve that person. It's predicated on a conversation. You have to get together with your users, you have to do interviews or anthropological studies to understand exactly what will serve these people... That's the heart of how a lot of design is done today.

I looked up your process of ethical sales, and it also seems to be predicated on a conversation, as you said, between the customer and the salesperson. One of the things I heard you say somewhere else was: "If you want to be interesting to people, be interested in them." This reminds me of Dale Carnegie in How to Win Friends and Influence People – an amazing book I'd recommend to anyone. But we'll talk about books in a minute, so if we stay on the topic of design and conversations...

In design, sales is very obviously relevant in two places. First, you need to find employment. You have to sell your work to clients; or to a company, to get on their staff. But, second, designers create things that sell at scale. The purpose of most design work today is to sell something using a visual language. Since you've been a copywriter, you also have this experience. So how do you have a conversation and show interest in the customer at scale? How can we apply your framework to copywriting or graphic design?

I have this LEAP model for marketing and sales: you Listen, you Explain, you Ask, you Profit. It starts with listening, not just because Dale Carnegie wrote about being interested in people. It's because, unless you take the time to research what is important to the other people, their fears, desires, wishes, wants, aspirations, their frustrations... How are you going to present a message or design a visual representation that's going to click with them?

So in a sales conversation, you want to ask a lot of questions and really listen, intently, and try to figure out what the other person is like. If it is remote, if there's a screen in between, then your research still has to happen. It's just, you need to find different ways to do that exploration. So no matter what it is that you are trying to sell or convince somebody of, you always need to take a lot of time to figure out what kind of conversation is going on in somebody's head.

Everybody has a conversation in their mind, an internal dialog. Your goal in business is to become part, to be included in that conversation – to join the conversation going on in the other person’s head. And there is no other way to do that than to research. Whether you read piles of marketing reports and studies, or you have customer interviews, or you use surveys... There's all kinds of ways that you can show up to the existing information, drink that in, and start to learn the other person.

This is the the major mistake that I see people make – it goes for copywriters, designers, coaches, consultants... Nearly everybody assumes that what they think the other person needs is actually what that person wants. But then, you're operating and thinking communicating from inside your own bubble. And some people will say "yes." They will pay you, or they will click, or download... But a lot of people will feel, "it's not really for me." And then you lose. So: research. Study people. Become a fascinated, deeply curious learner of others. Become an anthropologist.

Perpetual study into what life is like, for the other – that's the only way

One of my favorite books for designers is The Ten Faces of Innovation by Tom Kelley from IDEO, one of the most successful design companies in the world. He describes the roles or competences you need in a team, for successful design and innovation projects. The very first one is "the anthropologist." It always begins with understanding people you design for.

Your framework resonated with me, because it's what I have been applying in various conversations like job interviews, or meetings with prospective collaborators. I rarely go in having pre-decided that we are a good fit, that I really want this to work. I go there to figure out if we fit or not. Most of the time, in fact, we do not. Perhaps we can circle this back and treat sales conversations like that. Ask yourself: "Would I like to have an enduring relationship with this client?" If you're there to make the sale and be gone forever, then you can use whatever tactics, to win. But if you treat it as a continuous, long-term, positive sum game; that increases the quality of your engagements.

On the topic of jobs: you seem to have led an extremely creative life. From your resume it seems like you have reinvented yourself many times. You've been a monk, living in a monastery for 12 years. You ran a bespoke tailoring company – a shop where you produce formal clothing like suits and blazers, hand-made from scratch for the customer: a luxury craft service. Then you took up copywriting. And currently you serve as a sales and marketing coach. I have also read that you are an illustrator and singer, and I've heard that you had a period focusing on art marketing. This is a very rich life – so many enviable creative experiences... Most of us stick to one profession for all of our lives; it's uncommon to lead a life like yours. What have you found the most rewarding in reinventing yourself multiple times, and is there anything that you feel you might be missing out on?

Well, you call it reinventing myself. From where I stand, I just have trouble figuring out what to do with myself. I experiment. I learn. I try to figure out how this thing called life works, and where I can thrive most, and serve most; and where there's new things to learn, that create new opportunities, relationships, or possibilities... It's just the consequence of being being insatiably curious, having a passion for learning, for experimenting; and letting life guide me. I end up making choices that may or may not be wise, but they all bring me experiences and growth; and then that leads into something else...

It is a very beautiful experience. But it is also frustrating, because what it comes down to is that I have trouble focusing. I can fall in love with something new in the space of an hour and that becomes my main thing for months.... I always thought that I can't draw. "I can't draw a stick figure to save my life" – this was my saying. These days I make illustrations, and what do I draw? Stick figures! It just happened – I needed to illustrate this presentation. I didn't want to go and look on stock websites. "I'll just draw a couple of things myself – how difficult can it be!" Then, people started helping me and giving me advice, and it became a thing, and it became fascinating. Then my coach said: "You should draw portraits. You should copy an artist, every day, for three weeks straight" – because he saw something in me that needed to come out and develop. So for three weeks I spent the entire day working with charcoal, copying portraits made by other artists; just as an experiment to see what would happen.

What happened is that I made some portraits, some drawings, that really shocked me. They looked alive. I had never thought that I was able to draw anything beyond a stick figure – I didn't even think that that is something I could draw!

And this just to illustrate... I have a business to run I don't have time to spend three weeks... But that's what I did, because I fell in love with it. That's what keeps happening: I find an idea, it becomes interesting, I convince myself it's the right idea, and then I go into it full-on. Like with the tailoring business: everybody was telling me, "be careful, you don't have the experience!" I thought, well, I make really good suits, so I should be able to do this and make it a success. And I just jumped into it.

Well, three years later, I'm completely bankrupt. I need to do something. I had always done translations in the monastery, so I had a linguistic ability, I used to write. I thought, "I'll just go and write some articles!" Then I was asked, "can you do sales copy?" By now, we're talking 3-4 years as an entrepreneur. I'd learned a lot about marketing and sales, so I took that job. They were very happy, and sales copy became a thing.

Then I realized that I'm selling people a tool and most people who buy it don't know how to use that tool. They drive the wrong traffic at it, or it's on a page that is never going to convert... So I should start teaching people how to actually do their marketing better! I transitioned from copywriting to education, did that for a while. Then I thought: artists. Artists need help – oh boy, is that a niche that needs to learn how to market and sell. So I worked with artists for a while.

I actually spent the last few years trying to figure out who I'm for. Who is actually the sort of person that I want to work with? So, it's just this natural progression from one event and one experience to the next. I try to listen to life, go along with what seems to make most sense, and try to not be blinded too much by my falling in love with things, which is difficult.

Every single item on your resume is fascinating to me, for different personal reasons. First, the monastery. I haven't spoken or written about this much so far but I have been practicing yoga and meditation for the last 10 years. I started as a grad student: I would take breaks from the research, sit in the garden outside our lab, and read these books like Shunryū Suzuki's Zen Mind, Beginner's Mind and Ajahn Brahm's a handbook for meditators. I have even trained as a yoga teacher. But I have never taken the step to immerse myself in an experience with a long duration, not even for a week. For example, I've never been on a retreat. What drove you to becoming a monk? Did you experience something that led you to that path?

No, not so much. When I was in my teens I had no real spiritual orientation; certainly had no belief or faith. I always considered myself an agnostic. But then I met people who meditated. I started to join, and I found it very beneficial. It started to do a lot of good things for me. And I just went on on blind faith: "Hey, meditation is good for you. You can sit with us, if you like." OK, I'll give it a try.

Over time I became more involved. I would go more often. Then I would go and stay the night, and help out with the kitchen, and the painting, and the translations... In the end, I would be there almost all week, until it made sense to just move to their different city and live closer.

Around that time, the idea of an actual monastic community started to form. So I started to live as if I had taken the vows, just to experiment. And that gave another deepening of my experience. So it was a very natural next step to end up taking the vows and becoming an actual monk at some point. Again it's just listening, seeing where I can grow and benefit most.

Can we learn more about the particular order, monastery, or teacher that you studied with; the group that you joined? Do they have a particular name? Have they published books?

Yes there there are many books. I don't typically go into details publicly. I don't know if that is something i should change.

That's common. When I studied yoga teaching, my teacher never spoke about his lineage. The last time I studied with a new teacher in breathwork classes, she didn't want go into much detail either.

I think it's because, when you become interested in these things, you assimilate and synthesize so many different sources. Even people who affiliate with a particular order or teacher continue to learn from other teachers, and resources, other schools of thought... People ask me what kind of yoga I do, and I like to say, there are as many kinds of yoga in the world as there are teachers. I have my own "brand" of yoga that I practice by myself. It's hard to delineate schools of thought when it comes to these things. These, I guess you could say, Eastern schools of thought or these philosophical schools – that's not the way they work. It's not like Western science where your citation graph is clear, and it's clear where every idea is coming from – whose lab, which experiment, which study...

Do you still maintain any regular practices that you began as a monk?

I meditate in the morning. I spend half an hour in silence. That's about it.

My life changed very dramatically when I left. On the outside, you know, I live a normal life. I go out, I do all the "wrong" things. On the inside, nothing has changed. You can take a monk out of a monastery, but you cannot take the monastery out of the monk. So for me, in my experience, everything is just the same. I don't meditate seven times a day anymore, but I'm still the same kind of person; with the same values, and mission, and desire to serve.

So let's get to some of those changes. I think tailoring was the next step.

I find tailoring really amazing because there are so many techniques in tailoring that are not possible to replicate with a machine. You know, most clothes are produced in factories with machines... I know this because my father was in the clothing industry. He's mostly retired now, but he used to design and manage factories for making suits, shirts, jackets, and so on. And the hand-made jackets and suits are a different story. There are so many techniques which are applied in these garments, where certain shapes and styles are not possible to manufacture with machines – they have to be done by hand.

How did you become involved in this line of work? Were you the craftsman, or managing the store?

We were starting a monastery, and we needed a uniform. So we designed a shirt, trousers, and a jacket, you know, to be our brand. And now somebody needs to make this – because, you know, a monastery isn't typically a very wealthy organization. So we can't go to shops and have this made.

"Martin, you know how to use a sewing machine! Why don't you go and search for a tailor, and learn how to make this? Study making clothing!" I dutifully went and learned from an old guy in the Hague in Holland. He taught me how to make these clothes.

Then I thought: "Actually, my teacher says that I'm talented, that I'm good. So why don't I also learn how to make business suits, because we can sell these! I can do work that supports the community!" So I started learning that. Again, this is one of those examples where I fell in love with an idea, even though people were saying, "we need your help with translations, this is a waste of time, we don't want to sell suits..." "No, believe me, I can do this, this is worth a lot of money, we can fund our development!" So I learned, in addition to our own clothing, how to make high street, hand-made wear.

When I left the monastery the most logical thing to do was to just set up shop and try to make a living. It went really badly. Oh, it was such a disaster. But I learned from that. It was a 150,000-dollar MBA – that's what I call it. My dad died in the year after I left, so I inherited 150k, and I though: "Now I can invest! With money you can make money!" But because I didn't know anything about business, and I didn't want to do any marketing and selling, I blew through that money. I was not a qualified business owner. So it was an abysmal failure, but it was the best school. You cannot purchase an experience like that. It was really tough, and it was a disaster; but what I came away with was a schooling that has served me to this day. I don't regret it. I mean, I'd rather have my dad than a bankrupt company behind me, but this is how life is and it's been a real growth process throughout.

I'm not sure if it generalizes, but my experience in design and craft is that it's very easy to not be able to deliver to the client's expectations. What you're selling, the product that you're obviously custom-making for the person, doesn't exist at the start. So it's hard to materialize what the client has in their head. So I spend a lot of time trying to come up with ways for how to communicate. When I teach to upcoming designers I try to teach ways of communicating with clients: how to capture and materialize – in stages of increasing fidelity or increasing resolution – someone else's intentions in a design. Was that part of your experience?

To what degree will a client know what design is the right design? What can we define now as an outcome that, once it's ready, you'll sign off on? That is a very difficult thing to do.

I'm thinking now of the Clients from Hell website... I don't know if you've seen it – where feedback comes back and it says, "can you make a pop more?" Like, what even are you asking for?

I have seen it, first-hand. I've also given it, first-hand. (Laughs.)

I mean, what do you say when somebody comes back like that? And why do they come back and say something like that? First of all, it's possibly because you shouldn't have taken on that client to begin with. Somebody who ends up asking something like that can be identified at the start, and somebody who asks, "can you make it pop" – it doesn't sound to me like a client that you can ever satisfy. So that somebody that you want to be able to identify and filter out, right at the start. And there's ways to do that. You can ask specific questions, that help you understand if this person is quality client material or not. And if they are not, you shouldn't want to work with that person. Then you end up with quality clients.

Now you need to figure out what exactly it is that they want. When a client comes to you and they tell you they are hiring a designer, what is this client buying?

That's a good question. When the topic of sales, marketing, and business comes up in design circles so in the business of design – which is mostly service business as opposed to product business; and it's mostly a landscape of smaller companies, agencies and such – this is usually the crux of the conversation. What are you actually selling to these people, and how do you communicate it? There's a really great, kind of, master of this: his name is Chris Do, and he has this organization called The Futur that does business education for designers – they were a an inspiration behind Design Disciplin. He talks about the same things: How do you figure out, what does this person actually want? If you don't figure that out, then you can never satisfy this this person.

You can only satisfy the client if both you and the client are clear on what it is that you're trying to satisfy. Something "looking good" or "popping" – these are not measurable criteria. You need goals where you can look at the product or the results that the product leads to; and you can see in the numbers, the shapes, or whatever you're looking at, if they are satisfied.

But even before you get to see that data, the client needs to say: "Good, we're done here! I'm signing off on it!" It is not measurable. And very often, a client will want something that is against their best interest. Same thing with copywriting: very often a client will say, "yeah, I don't really like it!" That doesn't really matter. The ideal reader, the person that you want to connect with – do they like it? Will it click with them? What you like might be completely different from your ideal customer. If I turn the copy around and turn it into something that you like, I might have just killed the entire project: no sales, no sign-ups...

Subjective being pleased of the client, that satisfaction, is not necessarily a good criterion for saying it's ready and it's right. I see a real challenge there for designers in how you have this this conversation. So you go back to the question: what is somebody really buying right now? You said, "the crux is what are we selling people" – but that is not the question. What you're selling is different from what people are buying. What does somebody ultimately achieve, when they buy something?

Steve Jobs said: "People don't buy products, they buy better versions of themselves." That's where you find the solution. Everything that we do is a way of signaling to other people who we are – what we care about, what we stand for, what we would stand against... That stems from how we see ourselves. "I am the ethical selling coach, and I stand for that, I will help people who deserve to do well so that they get to serve better..." That's Martin's identity. Wonderful.

Any time that you do something, including everything that you purchase, it says something about how you see yourself in the world, and how you see yourself relating to the world. When somebody makes a significant decision... You know, buying a phone case is a trivial decision and a trivial identity consequence; but if you buy a new website design, for example, that is a much more weighty choice to make. So when somebody spends 5,000 or 15,000 on a big design package, what does that say about them? What kind of different self view do they purchase, when they give you that money? That's where you have to start.

When you have sales conversations with people, you want to figure out not just what is the concrete, visual, effect-generating deliverable that they're purchasing; but also what change in self-view that signifies for them. Once you have that, then, figuring out what is required to fulfill that change in self-view that they're looking for – that becomes a much easier job to do. So now we're really looking at the deeper workings of psychology: how somebody sees themselves relating to the outside world, what story they tell themselves about themselves and their role in the world, and their relationships...

If we try to put that in a framework... Let's take the side of the client – someone who might be buying a service; a design, whatever... One of the considerations is: what result is this going to generate for the business? Another consideration is: what result is this project going to generate in terms of their self-view? If they can align those things, they win. And as the other side – as the supplier of services, designs, or coaching – if you can align those two same variables on your side, as well as the considerations on your clients side; then everyone wins.

And it doesn't have to be that difficult. People get themselves all worked up and and bent, trying to figure it out, to converse with the client in such a way... Just ask questions. Be interested.

Do you have any experiences in terms of identifying people whose self goals and business goals are aligned versus not aligned?

The first thing that comes to mind is my business partner. I'm starting an agency with a friend. He's never been an entrepreneur, he's a lifelong employee. Because of last year's situation, his office was closed – he runs a co-working space. Suddenly, he was at home and bored, and I said: "Antonio, this is the time. We've been talking about this for years. Let's do this. Let's start something together."

For him that's a big choice, a big step; because it requires all kinds of decisions, habits, and actions that he's not used to. To be a self-sustaining production machine – if you've always been an employee, where are you going to find that entrepreneurial spark? So i had to find a way to have him want to step in to the role, the identity, the partnership, the collaboration... He used to be a finance man, a stock trader. He left that behind years ago. These days he just really would like to spend time with nice people, help them, and share from his knowledge. So, for Antonio, it was a matter of developing activities and attitudes that enable him to be more generous and helpful.

What are some books that you recommend the most to people that you work with?

For negotiation, try Never Split the Difference by Chris Voss.

Pitching: Oren Klaff, Pitch Anything.

I have read that one. His attitude is totally different from yours.

Yeah, very different, but his way of looking at the process and composing messaging that works for people is very useful. I'm not endorsing anybody's views or politics or anything, I'm just saying that he says things that you can learn from.

For psychology – especially for the psychology of dealing with costly sales, high-ticket sales – Geoffrey Miller, and the book is called Spent... Sex, consumption, and evolutionary biology or something like that... He really dives deep into why, on a very fundamentally psychological level, why we are motivated to do things.

Jay Abraham, Getting Everything You Can Out of All You've Got – that's a really good book.

What places and tools do you spend most of your time with these days? And tools – perhaps places too – includes software.

I like to be at the beach with my laptop, and just do my work.

When it comes to tools I use all kinds of things... From Slack to Telegram, to Opera browser – people laugh at me, because I should use a more modern browser, they say. I like it. Get off my back. (Laughs.)

I use Thunderbird – which again, apparently, is not something you should say, but I like it...

There's nothing really specific. I find whatever tool is easiest to implement for the job to be done at the moment.

Do you know what is next for you? Anything that is exciting for you, that you're intending to go into in the near future?

I'd like to start a podcast. There's a bit of an opportunity cost there, so I don't know if that is something I'll be doing soon.

Next is trying to get our agency to success. We started with a completely new focus a month ago. We're doing customer interviews right now. We're getting some good feedback, and some really valuable insights. So we hope to take that to to revenue. We've been trying for a year to launch this thing, but we kept trying new things, a lot of experiments... So now it's like, OK, we're going to be working with bootstrappers, and that is the kind of person that we want to talk to. So to get that up and running, that's next. That's what we're working on.

Those are all the things I have to say. Anything you would like to add?

Whatever it is that you're trying to achieve and figure out, in business, or sales , or marketing... Don't take yourself so seriously.

We we get all stuck in our heads, thinking about how important it is. This is only your ideas. This is the way you configure your view on the world, and then you make that a big thing that needs to be satisfied. Then you're taking yourself much more seriously than you need to.

Chill out. Just have a conversation with people. A buyer is often just as anxious as you are: "oh, they're going to put pressure on me, and it's going to be so expensive, and then all the decisions that I have to make..." They need help. When you're selling to somebody, you're there to help them. So just have a conversation with people about, what is the best decision for you to make at this moment.



Connect with Martin Stellar

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