In short
Prof of AskOkey (formerly a banker) discusses reinvention and identity, arguing that dressing well shapes mindset and presence, and that personal “character” is built through resilience, philosophy (especially Stoicism), and purpose beyond money.
Guests
Prof (AskOkey) is a former investment banker who started with a WhatsApp blog/group (grew to the WhatsApp limit of 256), then launched YouTube around 2017–18. He later took a break (2018–2020) to design his tailoring brand, AskOkey, starting with trousers. He describes a life of hardship after his father’s assassination and his mother’s early death, including years of menial jobs in Cleveland, Ohio, before business school and a J.P. Morgan role.
Key claims
Clothing can function like “the cover of a book,” influencing bearing and self-concept. Identity is “absorbed” through lived experiences, not copied. Contentment is a “final boss” state, but ambition must be channeled toward loved ones, mentees, and community. Grit can’t be engineered into children; values are transmitted by example.
Notable examples
His “shoes on” effect on voiceover/writing; reading The House of Morgan to outperform interviewers; day-laborer and multiple jobs in Cleveland; using his brand to provide direction for young men.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Power of Dressing Well
1:39 to 3:00
Explore how clothing impacts self-perception and confidence.
“Before we turn the cameras on, of course, I was admiring the way you look, the way you're dressed, and the way you're held, and the presence that that created in the room.”
Prof's Journey from Banking to Tailoring
3:00 to 6:40
Understand Prof's transition from an investment banker to a tailor.
“But if I put my shoes on, my voiceovers sound a lot more eloquent.”
Building the Ask Oki Community
6:40 to 13:30
Learn about the emotional connection within the Ask Oki community.
“Can you please tell me more about what came first and what the Ask Oki world has going on today?”
The Transformation of Prof: A Personal Journey
14:02 to 16:48
Learn about the transformative journey of Prof from a different background to becoming a symbol of style.
“on my Instagram, which I tend to be more present, especially in the early days when it was a smaller group and I was a little bit more involved day to day.”
Loss and Resilience: Overcoming Life's Challenges
16:49 to 21:06
Explore the challenges of losing family and how resilience shapes identity and business.
“I think I might have been 21 years old and someone gave me this book.”
From Day Laborer to Wall Street: A Career Breakthrough
21:07 to 24:42
Discover how hard work and determination led to a successful career on Wall Street.
“And so I did take the GMAT and all of that stuff.”
Assimilation and Personal Development in High Society
24:43 to 28:00
Learn about the process of assimilating into high society and the importance of personal development.
“I was I got, you know, I was offered the job.”
The Scramble for Knowledge
28:00 to 29:25
Exploring the necessity of learning for survival and personal development.
“Because I didn't have, I didn't have like, you know, a father who went to Phillips Exeter, or went to Harvard, or Yale, or this or that, you know, could pass down this knowledge and tradition.”
Philosophy and Stoicism's Impact
29:25 to 31:10
How classical philosophy shapes character and identity.
“So I started studying things like philosophy, you know, even within philosophy, beyond the classics, stoicism.”
The Role of Clothing in Identity
31:10 to 33:19
Clothes as a reflection of identity and personal growth.
“experiences that I myself have had to endure over the course of a lifetime.”
Show all 24 chapters
Driving Forces Behind Ambition
33:19 to 36:54
Understanding the motivations behind ambition and personal legacy.
“Because our own selves are not reason enough for us to summon these supernatural powers that allow us to overcome impossible odds.”
Reflections on Life's Purpose
36:54 to 39:43
Contemplating life’s work and its impact on future generations.
“And if my life has been devoted to creating a stage where they can display or sort of their talent can be acknowledged, then maybe that's a life worth living.”
The Irony of Wealth and Desire
39:43 to 42:00
Discussing how wealth changes desires and life priorities.
“dream of the moment you could ask yourself that question?”
Reflection on Wealth and Fulfillment
42:00 to 44:10
Explore the speaker's thoughts on wealth, materialism, and true fulfillment.
“If I sold my company today, if we sold out and I came into an enormous sum of money, I honestly, frankly, I'm not sure how it would change my life.”
Balancing Contentment and Ambition
44:10 to 46:20
Discussion about the tension between personal contentment and ambition in life.
“stupid money on material things just to gain their approval.”
Fatherhood Expectations and Responsibilities
46:20 to 48:32
Delve into the speaker’s perspective on raising sons and the responsibilities of fatherhood.
“For instance, I sit here, I just told you about sort of how I feel my life is today, where in my own personal life, I feel content.”
Navigating Parental Guidance and Independence
48:32 to 53:38
A conversation about guiding children while allowing them to forge their own paths.
“My oldest son is a math major with a minor in computer science.”
Understanding Grit in Different Contexts
53:38 to 56:00
An exploration of the concept of grit and its varying significance across experiences.
“Based on everything you're telling me today, Cleveland is such a big part of who you are.”
Understanding Grit and Resilience
56:00 to 1:00:00
Explore the concept of grit as a measure of resilience and how it can be instilled in children.
“And, you know, grit is in many ways velocity.”
The Invaluable Gift of Example
1:00:00 to 1:03:20
Learn about the importance of parental example in shaping a child's identity and confidence.
“Just that sense of who you are, giving your kids, at least I acquired from my own father, that sense of who I am.”
Desire and Personal Growth
1:03:20 to 1:06:40
Discover the role of personal desire in achieving one's highest self and aspirations.
“of a quick pep talk from you for the rest of their days today.”
Fashion Tips and Personal Style
1:06:40 to 1:10:00
Get insights on modern fashion choices and what to avoid to look your best.
“And that knowledge, basically, four years later, has landed him where he is today as a head of design.”
The Lesson of Authenticity
1:10:01 to 1:14:20
Learn why being yourself is crucial for success and fulfillment.
“And better still if you get them from Ask Hoki.”
The Cost of Ambition
1:14:21 to 1:16:38
Explore the sacrifices required to achieve your dreams and reflect on their worth.
“I think fantastic on a personal level, right?”
Transcript
Automatic transcript. May contain errors.0:00Today we helped a latte for Sam coffee shop get an insurance quote simply and easily and made sure a floral delivery van was able to make someone's day. We're the Hartford with decades of experience insuring millions of unique small businesses. When it comes to your small business insurance.
0:20The Gstaad Guy:Thank you. One size absolutely does not fit all. Get a quote or find an agent today at the Hartford dot com slash small business. This episode is brought to you by Indeed. Stop waiting around for the perfect candidate. Instead, use Indeed Sponsored Jobs to find the right people with the right skills fast. It's a simple way to make sure your listing is the first candidate C. According to Indeed data, Sponsored Jobs have four times more applicants than non-sponsored jobs. So go build your dream team today with Indeed. Get a$75 Sponsored Job Credit at Indeed.com slash podcast. Terms and conditions apply.
0:58The Gstaad Guy:I'm really excited for this episode. Very, very excited. Thank you so much for being here, Prof of Ask Oki. When you walked in today, I was seeing everything I expected from your videos. Just for those who are dialing in audio only and are not tuning in with the video, I urge you to check out what the video looks like to see this distinguished gentleman to my left and see how he's dressed. Thank you, sir. Thank you for having me. Thank you so much for being here. Thank you. Around the world with your host, the Stade Guy. We welcome you back to the Stade Guy podcast, sharing stories of excellence with those in the know for those who just know.
1:42The Gstaad Guy:Before we turn the cameras on, of course, I was admiring the way you look, the way you're dressed, and the way you're held, and the presence that that created in the room. I'd love to start there with the amazing aura that that holds and the presence that creates which naturally comes with intention because it's not easy to look this good, as you know Well, are you seeking my response or are you asking how do you generate such an aura? It's both I don't know that there's a straight answer to it Shall I call you Constance or shall I call you Colton? Today I hope to be Constance. Today you hope to be Constance.
2:29I hope to be Constance. I don't know that there's a secret formula to it, but I think that it was Niccolo Machiavelli who said in his book, The Prince, that each time he went up to write, when he was writing the story, he dressed himself in the robes of silk and gold. and there's this idea that when you dress yourself or you sort of you clothe yourself in a certain way you become a different person like literally you carry yourself a different way you think yourself think of yourself a different way and so when you dress like a king at least you try to dress like one you carry yourself like a king because they go together so I don't think I think again for me I don't know if that applies to everyone but I think it's been proven to work through ages that the way you clothe yourself or the way you adorn yourself has a direct impact on the way you you carry your bearing on the way you carry yourself
3:31The Gstaad Guy:i absolutely feel that i do a lot of my my work and recording from home and i could be fully dressed but something as simple as putting my shoes on because at home i don't usually wear shoes. But if I put my shoes on, my voiceovers sound a lot more eloquent. My writing is a lot more eloquent. This is a very strange thing, you know? So I see it. So today you're wearing this beautiful double-breasted wide lapel beige suit. Please tell me more about it. So this is what you I'd call, this is what in our Sartoria parlance, we call it Solaro. So the fabric itself is called Solaro. It's sort of like a herringbone.
4:16Again, I want to sort of really stay away from talking shop because I have to be reminded I'm not on my channel where sort of I'm surrounded with a lot of Sartoria heads speaking to a broad audience. And so Solaro is a summer fabric that is produced by one of our suppliers, our skoki suppliers, Harrison's of Edinburgh, their 200-year-old male. And Smith Woolens is one of their brands, and they started producing this cloth, Solaro. And the idea behind Solaro is to sort of to keep you cool when it's warm. It's got reflective properties. So if you look at it, it's like a herringbone, but it's got the sheen and shine to it so that when you wear it in warm climate or sort of under radiation sun, it reflects heat and it keeps you cool.
5:10So that is what I'm wearing is a Solaro suit. I love it. It usually comes in tan. That is a natural color of Solaro. Now they make it in other colors, but this is a natural color of Solaro because tan has that reflective quality that sort of pushes away radiation. So that's for my suit. My shirt is a linen shirt by one of our suppliers, Calo Riva. Calo Riva is an Italian meal. I would say sort of the Rolls Royce of shirtings in the world. No pawn on Loro Piana, who I know you love. For those of you out there watching, Mr. Loro Piana, if you're watching, Boccalo River, they are a shirting maker, not to be mistaken for a shirt maker.
5:59A shirting is the fabric that is used to make the shirt. So they're based in Italy and And they make the finest, in my view, quality fabric to be converted into a tailored shirt. So we tailor the shirts at Ask Oki, but we source the fabric from Calo River. So that's my shirt. And my tie is just a beautiful paisley tie that I've owned for quite a few years. And that's the pocket square.
6:30The Gstaad Guy:So I know you through your content, first and foremost. I've slowly learned that you also have an incredible tailoring boutique, an arm of your business. Can you please tell me more about what came first and what the Ask Oki world has going on today? So we started, you mean sort of the brand Ask Oki? Yes. So before the clothing came along, I was, you know, I guess you could call me a blogger. Yeah. I used to be an investment banker, as you know. And when I decided to take early retirement from banking in 2017, I had a WhatsApp blog, a WhatsApp group. It was just on my phone, just basically a WhatsApp group.
7:14I invited a few people, five people, and I would write daily on different subjects, right? Philosophy, economics, macroeconomics, markets, and clothing. Just to five people? It was started with just five people. Wow. It was just five friends, right? For me, it was just a creative outlet, just sort of people who read my stuff and then maybe respond. And then the five people started inviting their friends. They would invite, oh, can you add my friend to this group? Can you add my friend? And very soon, that broadcast list became 256, which is the maximum number you can have on WhatsApp. And I couldn't add more people, but there was a lot of demand.
7:56People wanted to read the stuff I wrote every day. This was around 2016, 17, right? 2016, 17. There was a lot of demand and appetite for my content, whatever I was writing. And what would I do? Sometimes I'd get up in the morning, dress up, right, to go to work, right? And I would talk about what I'm wearing and why I'm wearing what I'm wearing. Sometimes I would go into some detail about the fabric or whatever. Well, that's it. For me, it was just a creative outlet. And so when that list grew beyond 256, they said, well, you've got to go public with it. You know, you have to start a YouTube channel.
8:33I'm like, I'm not starting a YouTube channel. You know, I enjoy my privacy. I don't want to go public. And so they pushed me for, and I resisted this for a long time. You know, I wasn't sure if I wanted to sort of have myself become a public persona as you and I are today. I fought it for a very long time. You know, obviously, we all have cobwebs in our wardrobe, in our closets. And I'm not sure that I was ready for people to start prying into my private life. But, you know, be it as it may, I think eventually I relented. I did relent. And I started a YouTube channel around 2017, 18. They were very amateur videos.
9:19They were done on my crappy iPhone. with not even a mic. I would just sort of record things in my studio, talk about fabrics, talk about shoes, talk about this, and I would just upload it. I would edit it myself. I mean, some of them are still there. They were really crappy videos. But, you know, sooner or later, I had 500 followers. I'm like, okay. And then, well, subscribers. And then it became 1 ,000 subscribers. I'm like, oh, my God. You know, a thousand people, you know, like, you know, this is, I'm famous. And I think the day it really hit me was one day I was in the mall. I was taking a walk in the mall and somebody came to me, you know, who eventually became my first customer.
10:05He came to me and was like, you're the guy on YouTube. I'm like, ho, ho, ho. Like somebody, like, I was like, literally it was the first time I was identified in public by anyone who didn't know me. and like you're the guy on YouTube and then we struck up a conversation and then he actually eventually became my first customer um but yeah that's how it started it started with the YouTube channel and then that 1 ,000 subscribers became you know 2 ,000 subscribers then at a point I said whoa whoa whoa whoa um this is growing and if I'm gonna do this I'm gonna do it right right i didn't i was sort of fed up with shooting the crappy videos on my iphone and without editing proper editing so i took a year off uh actually two years off between 2018 and 2020 in that time i had started to sort of play around with design ideas for ask okie i started with trousers you know i literally went to my studio and started creating a pattern myself on my hands and niece.
11:16My friends thought I'd gone crazy. You know, why would you sort of leave a career in investment banking to go become a tailor or to go sort of try to pretend to become a tailor? They couldn't understand. And I think I couldn't even understand myself. But I started in that time that I took a break from YouTube, right? Between 2018 and 2020, I was creating the product. I started with trousers. I drafted the pattern. I found a tailor. I said, listen, I have this idea, right? And I am looking for sort of to partner with sort of a tailor who can actually sort of execute on my ideas. And so that's how we started.
12:00We created the first pair of trousers and I wore them. I took photographs and videos and I showed them to my WhatsApp group. This was my kind of market that this time was like 200 people. And I showed it to them. And some of them, it's like, hmm, interesting. Can you make us one? And I'm like, I suppose I could. But then these guys were all over the place. They were in the U.S., in Canada, in Europe, in Asia. Like, my WhatsApp group was global, right? So these are sort of people I'd met all along the way while I was a banker, right? So people dispersed all over. I'm like, okay, how do I fulfill these orders?
12:41That was the first challenge. I mean, they all can't come to me. So how do I create this product for them remotely? That was how the idea of Ask Okie was born.
12:55The Gstaad Guy:While creating those products for them and communicating with the initial WhatsApp group on all these different topics and categories, it doesn't seem so far off to a lot of your storytelling today, which of course a lot of it is connected to the way one dresses, the amazing things you make. But there's also so many layers to your conversation online and a part of why I enjoy your content so much. You don't just talk about the what, you talk about the why, talk about the how. You talk about the effects those things can have over a long period of time. Where I'm going with this is I'd like to understand what the Ask Okie community, what they're looking for when they engage with you, possibly at an emotional level, much more than just a beautiful pair of trousers that you came up with.
13:48I think for Ask Okie, a lot of, especially the younger followers, they are seeking direction in life, right? They see my life story, which I've shared numerously. on my Instagram, which I tend to be more present, especially in the early days when it was a smaller group and I was a little bit more involved day to day. You know, I talk about sort of how Prof became Prof. You know, Prof wasn't always this sort of well-dressed, dapper guy who's this and, you know, with a Wall Street pedigree and an MBA and two engineering degrees and all of that stuff. I share, I open up every now and then a window into my own personal struggles and the challenges that have led to what we all see today.
14:48And I think that's really what draws a lot of people is the, shall I say, personal or philosophical side of what we represent. And when I say what we represent, meaning sort of my own personal story because I am sort of the face of the brand, so to speak. And so you find that a lot of young men today are looking for direction. They're looking for direction. and in some ways maybe they find the clothes as a convenient excuse for them to stay close to what they see as a source of inspiration.
15:39I'm not sure if that makes sense to you. It does make sense to me and I actually want to talk more about one of the points you made about the things you stand for
15:50The Gstaad Guy:and them finding inspiration in that. And you also mentioning coming from a very different background than life to the one you lead today. As a listener of yours and as a follower of yours, there's sometimes thoughts I have in my mind that are not fully formed. And then you say them, or an author might say them in another medium. And when someone else says them eloquently, I realize, actually, that's kind of what I feel. But now that it's said so eloquently, I realize that's one of those things I stand for. And I'm curious to know what those things that you stand for are and that people you think find inspiration from and how they existed in your life and in your heart in the early days.
16:38The Gstaad Guy:For you to ultimately craft your business and ecosystem as an entrepreneur around those things you stood for that are now so inspiring? I remember mine. I think I might have been 21 years old and someone gave me this book. Everyone's read it. I hope everyone's read it. Think and Grow Rich by Napoleon Hill. I have not read it. I read that book and it was sort of like, it was an eye-opener. I mean, I was 21. I was just finishing my undergraduate degree in engineering, electrical engineering. And it just opened my mind to sort of a world of possibilities. So at that point, sort of like I said, OK, this is what my life is going to be.
17:23But then saying it and doing it is another thing. A little bit of a personal story like you. And I've heard from some of your interviews, not your podcast, but interviews of you had something of a somewhat privileged upbringing. You know, both my parents were very well educated. My father was an engineer with advanced degrees. My mother was a PhD from the University of Michigan. So my parents were very well educated and well traveled and well placed, what have you. I had a young life that was very promising. You know, it promised a lot. And then that changed so quickly. My father was assassinated suddenly when I was 19.
18:05and my mother died barely three years after that. And so in a span of three years, I went from, you know, sort of this kid who had sort of the future, everything laid out in front of him. And all of a sudden I found myself orphaned and burdened, not just orphaned, but burdened with three younger brothers to raise. And I was barely 22. Wow. And so that really changed the event and course of life. And I made a decision, a critical decision at that point. I had an older brother. We had a family business, which was my father's company. And he basically said, you can have the business. You can have the business.
18:52I'm going to start all over. I'm going to America. I'm going to start all over. I don't want anything. Just keep doing this. I'm going to go and start from the bottom. And so I immigrated to the U.S. and literally started from the bottom. I worked for a year or more, maybe two, three years, as a day laborer. This is what a lot of people don't know. How old were you when you did this? I was 22, 23. I worked as a day laborer because, as you know, when you come to the U.S., It's not like you can just get a job or especially if you don't have, you know, a U.S. undergraduate degree. I had an undergraduate degree from Nigeria until I came.
19:43Even though I was an electrical engineer, it wasn't like kind of like you could get there and just get a job and become an engineer. So I had to go through this period of two years or three years where I basically had to find a way to integrate into the system. And in that period, I had to do a lot of menial jobs. I worked as a laborer, like I said, on construction sites, earning like$3,$4 an hour,$5 an hour. There were days when my lunch was just basically a hot dog and a bottle of Gatorade in Cleveland, Ohio, tearing down crack houses. I would finish that job, and then I would go home at night at 6 p.m., change over, and drive Papa John's Pizza from 8 p.m.
20:27till midnight, four hours delivering pizza. Wow. I would go to bed at midnight. I would wake up at 4 a.m. in the morning. I would deliver newspapers for the plane dealer, for the Cleveland plane dealer, from 4 a.m. in the morning to 8 a.m. I would come back at 8 a.m., change, and then go for my construction work from 8 a.m. till 5 p.m.
20:49The Gstaad Guy:Wow. This was my life every day for about two years. Three jobs? Three jobs. I slept only four hours and had no life. and by a stroke of good fortune, I somehow stumbled an opportunity and a scholarship to attend business school. And so I did take the GMAT and all of that stuff. I did well, you know, and applied to business schools. I got accepted. I got a scholarship, and I went to business school at Case Western Reserve University in Ohio. And it was while I was at Case Western that I met a gentleman, Joe Salatini, who was at the time a very top guy, J.P. Morgan, was an alumni of the business school.
21:39He invited me to New York. And I remember so clearly, I had$200 to my name,$200 to my name. A round trip ticket to New York was$160. I slept in a hostel for four nights, like$10 a night in New York. Because I couldn't miss that opportunity. So I went to New York, invited me into his office at 60 Wall Street, interviewed me, talked to me for about an hour. And then after grilling me, he sort of, you know, brought in the head of HR and said, okay, you know, you go off with him. And then I spent some time with the HR guy. He asked me also the usual questions. He said, okay, we'll get back to you.
22:23So I flew back to Cleveland. I was in business school at this time, right? And I remember so clearly I got a call from this HR guy. He's like, we want you to come back to New York. But this time we'll pay for everything. So they flew me back to New York. I put me up in a fancy hotel and blah, blah, blah. Met with some more people. Okay, go back and we'll call you. We'll let you know. So I went back to Cleveland. And they called me again. They said, okay, we want you to come back and do what they used to call a Super Saturday, which is like a whole Saturday of interviews. I mean, you talk to like, God knows, like 10 different people, like a whole day of interviewing.
23:05But it wasn't just you. It was sort of the finalists from all the business schools. So I was invited to this Super Saturday and I got there. And there were all these kids from Harvard, from Yale, from Chicago, from Stanford, from this and that. And I'm like, holy, I'm cooked.
23:25Like, I'm cooked, right? And so we got it and there had to have been 500, you know, maybe not 500, maybe like 300 candidates. And there were only 25 slots. Well, 25 slots. And I was like, what are my chances? Right. Now, what I did, and I'll come back to your why, is that I knew I was really kind of coming, given my background, my everything. I knew it was a really long shot. So what I did was that I got this book called The House of Morgan by Ron Chernow. It's a biography of J.P. Morgan, John Pierpont Morgan. And I read, I mean, this book is thick. It's that thick. Right? That thick. I read it cover to cover.
24:15I knew everything about the bank. Everything. And so when I walked into that interview, besides the technical questions about finance and this and that, when I talked to some of the senior people, right, and we start talking about the bank itself, they're like, holy shit, you know more about the bank than I know. And I've worked here for the last 30 years. You know, so to cut a long story short, Constance, I ended up on Wall Street as an investment banker. I got the job. I was I got, you know, I was offered the job. I started as an associate at Morgan doing mergers and apposition in their energy group.
24:51And then life changed. I was making six figures. And, you know, I was barely 26, 27. Right. Life literally flipped. Wow. Completely. I mean, I went from a day laborer to making six figures, right, in my, at 20, and this was six figures a long time ago. This is like the pursuit of happiness. This was 20 years ago. This was 25 years ago, 20, 20, 20 years ago, right? More than 20 years ago, 25, 30 years ago, this was six figures, 25, 30 years ago. Not six figures today, right? That's how much I was making at 27. Wow. So it was a complete, complete, complete, complete transformation from where I was to where Anna was.
25:36And that really just opened up a new world to me, right? The world of the Constances, right? I didn't know these people before. All of a sudden, I'm sitting with all these kids who were groomed from day one to be here. The moment they were born, they were groomed to be sitting where I was sitting. They went to the 92nd Street Y in New York, which you may have heard of. It's like some fancy nursery school where it's like$50 ,000 a year or$100 ,000 a year for nursery school for kindergarten. They went to private schools. They went to Phillips Exeter or they went to Andover or sort of all the other fancy boarding schools.
26:19And then eventually to Ivy League schools. So there's a path, right, to get there. You just don't show up on Wall Street. No. You just don't show up, right? There's a path. And so I'm sitting with all these Constance characters, right, who've lived this life, right? You talked about your rich friend who owns a villa or a castle, who you said even if you taped his mouth, right, even if you were naked, you would know he was rich. Exactly. So this is the kind of characters I was surrounded with daily, right? These guys were just, they came from money, they came from power, they came from just sort of you know a long lineage of a pedigree yeah and so i started to absorb that world the way they dressed you know started to absorb and sort of like kind of assimilate really you know so even the suits thing right it was just from learning how do people from sort of like upper society right how do they dress what colors do they wear what is showy what is not You know, sort of all these subtle cues I started learning when I got to Wall Street.
27:25I started to associate with these constances, so to speak. To cut a long story short, you know, that whole cycle became a playbook for me for life, right? Because I had seen it happen. And I knew that if it could happen in one realm, it could happen in another realm. so the whole idea of resilience having vision right having a vision this is where i want to go this is where i want to be right and then having the vision the resilience right and a lot of that comes with personal development you develop yourself in so many ways physically you know i've always been a gym rat you know just as a way of keeping my mind uh saying you know studying philosophy, I was forced into sort of like, literally, when you have no one to teach you Constance, right?
28:18You're like a hungry, you're like, you're like, you're like this sort of like, almost sort of someone in the desert dying of thirst, like you're scrambling for water, you know, your scramble for knowledge becomes the scramble for water. Because I didn't have, I didn't have like, you know, a father who went to Phillips Exeter, or went to Harvard, or Yale, or this or that, you know, could pass down this knowledge and tradition. So you're forced into the position where you must learn to survive. Not learn to survive, but you must learn in order to survive. You understand? Big difference. Big difference.
Read the full transcript
28:57So for me, learning, it wasn't sort of this idea of like, oh, let me tell you about all the books I've read on philosophy, right? Or let me just sort of, It wasn't just party talk, you know, sort of party talk kind of thing. For me, it was a question of life or death. You had to know these things. You had to learn these things to survive at every stage of this game that you were sort of like catapulted into. So I started studying things like philosophy, you know, even within philosophy, beyond the classics, stoicism. I mean, I've read pretty much all the classics, right? You know, starting from work.
29:37Socrates didn't write much of anything, but Aristotle, Plato, the public, just all the classics I've kind of read, I kind of went through there and then sort of found my home in the Stoics. So Stoicism, Marcus Aurelius, Seneca the Younger, Epictetus the Lame, and all sort of like the great ancient Roman Greek Stoics. So I find that all of this, right, they sort of, how can I say, conspire to create a character, right? And these things happen in drips and draps. They all conspire to create a character, a thing that people find admirable and maybe drawn to. And so when I see the persona of prof on social media and what draws a lot of young men, especially to the brand, beyond the clothes, right?
30:38The clothes are beautiful, like I said, but there are a lot of beautiful clothes out there. They almost sort of see the brand as a gateway into finding their own identity. And that by staying close to the brand or staying close to me as an individual through the brand, right, perhaps by osmosis allows them to absorb some of these character defining experiences that I myself have had to endure over the course of a lifetime.
31:16The Gstaad Guy:The clothes, as an analogy, to me seem like the cover of a book. The books you read are the language for you to come up with this character and get a deeper understanding of what you want to learn from, what you want to mold for yourself. But the heart is what fuels everything, and the desires that made you even want to start reading and want to start getting into the things you're into today, that can't be taught, right? You can't pick up the heart and the desire from a book. I think a lot of that, based on what you've said, comes from a very unfortunate circumstance that I'm sorry you went through.
32:06The Gstaad Guy:But that drove you in beautiful ways that I'd love to learn more about. I'd love to know what your heart desired to seek that knowledge and growth. My mother died a very painful death of cancer, and I was her primary caregiver during her time of illness. and
32:40she like your mom, like everybody's mom she gave me a lot
32:48and I think and she was very young she was quite young, she was not even 50 my mother, my father wasn't 50 either they both died young and I think whenever I'm faced with an assignment in life,
33:12you have to ask yourself who are you doing it for? What are you doing it for? Because our own selves are not reason enough for us to summon these supernatural powers that allow us to
33:39overcome impossible odds. And for me, it was always about earning the almost like earning the right to be here. I'm not sure if this is coming out the right way. I want to know that I've done good work. In whatever it is I do, I want to know that I've done work that I can be proud of or that anyone can be proud of even when I'm not here. I think a lot about when I'm not here, Constance.
34:21Or when I'm no longer here. not so much in a sense of this idea of being immortalized in posterity because I don't really think anyone cares about you anyway after you're gone, they cry and then life moves on, but how has my life's work how does my life's work live on through people like this young man sitting here. I hired him right out of university and I've trained him for three years. I was even furious with him just about an hour ago downstairs for a slight error in judgment. But I asked myself, how can I live my life in a way that allows him not to go through the things that I have been through.
35:34And not just him, there's a few of them on my team, like him, young, ambitious, hardworking. I don't know that I do this for wealth or to get rich. I don't think so. I hope, I know it's cliche, but I've had a decent life. But considering where I've come from, right, I've had a good run. I've had a good run. Right? And let's not get into sort of defining what a good run means in a material sense. But even in a material sense, I've had a good run. So why am I doing this? Some days I'm not even sure I have a precise answer. And maybe I find consolation in saying things like I'm doing this so that, you know, people like Hashim and Tim and Alan and the younger ones on my team do not have to go through what I've been through to rebuild a stage for the world to acknowledge their talents.
36:46I've had to build a stage for 30 years for the world to see my talent. They don't have to do that. They're very talented. And if my life has been devoted to creating a stage where they can display or sort of their talent can be acknowledged, then maybe that's a life worth living. Rather than being defined by, like you said, the physical material things, which are not irrelevant. But if I can live on through their own successes, right, maybe that's the life that's been worth living.
37:43The Gstaad Guy:I really appreciate you sharing all this with me and with the audience today. It's not an easy thing to talk about and to bring up, especially with cameras on and microphones here. and I hear everything you're saying and I really appreciate you opening up. It's a tough one. Do you find yourself thinking about these things most? The whys, the big personal questions after a day or a moment of things going well or of moments of struggle? I think about them all the time. I think about this all the time. whether it's I mean I've been through so much right that everything now just seems like I mean you still work hard you still but I think there are very few challenges that I face today most of them pale in comparison to what I've seen or what I've been through
38:50but there are days you know where I sit alone which as an entrepreneur you'd appreciate this. You spend a lot of your time alone. Especially for me as a leadership figure. I have my teammates but he would tell you I spend a lot of time just alone.
39:16And you ask yourself, why am I doing this? And you find yourself sitting there in my library with my cigar.
39:27asking, what is the point, then, of all of this? What is the point?
39:40The Gstaad Guy:Did you ever, as a young man, dream of the moment you could ask yourself that question? I don't think so, because I was just in a desperate, I was perpetually in a desperate bid for survival. Right? You talked in one of your podcasts with one of your guests about this whole idea of the journey versus the destination and how, you know, the rich are able to afford the expense of idealism, of exploring sort of like, oh, it's about the journey. whereas sort of those who are desperate are all about the end. Do you remember that episode? Absolutely. Talking about problem solving. Correct. Right. And I really appreciate you watching that.
40:37And it struck me because, you know, when you're trying to survive, you're just thinking about the end. The end justifies the means, right? So you're just thinking about just how do I just get this thing done? Like how the fuck do I get out of this? Right? That's all you're thinking. As you get sort of more well-to-do and more get out of the Maslow's hierarchy, you can now start philosophizing about the process of becoming. These are all luxuries that desperation does not allow for. So to answer your question, you know, I think that perhaps the reason why I have the, shall I say, luxury of wallowing in such philosophical thoughts is because perhaps I'm not worrying about what I'm going to eat tomorrow morning or what I'm going to wear, which wasn't always the case.
41:36The Gstaad Guy:I mean, now you actually stop yourself from eating entirely. You eat one hour a day. So you're imposing that on yourself. The irony. The irony. You're imposing. You know, that's the funny thing about life. And I find this to apply across the board. When you can afford it, that's when you don't want it anymore. And I've seen it in my own life, right?
42:00If I sold my company today, if we sold out and I came into an enormous sum of money, I honestly, frankly, I'm not sure how it would change my life. And I sit down and I ask myself the same question every day. How exactly is it going to change my life? I am not going to go out there and run out there and buy a Rolls Royce or Ferrari. Because I've owned one. And I sold it. Right? I've had a Ferrari and I've sold it. Been there. Getting the newer version is not going to cure that itch. That itch has been scratched and it's gone. So when I think about it, I'm like, how will coming into sudden wealth?
42:48I don't, you know. So in many ways, you worked your whole life. You went through so much to be able to afford this moment. to be in this moment, only to get to this moment to find out that, you know what, I don't need these things to find, I suppose if you might call it fulfillment. And I'm not being facetious. I really sit down and I ask myself, and I sometimes I go with a pen. I look at all this wish list, right, that I drafted when I was 20 years younger. Oh, I want to have a private jet and this and that. Look, it'd be nice to sort of have those things, right? But it's not, they're not burning desires.
43:27You know, if I came into a huge sum of money, am I going to go buy a jet? Where am I going to go with it? You know, okay, go buy a Bentley or a Rolls Royce or this. Where am I going to drive with it? Who am I going to impress with it? So what is the point? I'm not going to buy these things to kind of stock my house up to look at them every day. Most times we buy things to impress people or to sort of to signal. And you get to that point where I just feel there's nothing around me worth signaling for. There's nobody for me, I mean, I admire people, but there's nobody around me that I feel the urge to impress so much that I would go do something as stupid as spending stupid money on material things just to gain their approval.
44:14I just don't feel that anymore. And for the first time, I'm in the position where I can actually do those things now. But I don't feel the urge or see the need to. So going back to your fasting example, it's like, I have a means to sort of feast on a buffet all day long, but I only eat once a day.
44:41The irony of life, isn't it? It's true.
44:44The Gstaad Guy:But honestly, when I think about the game of life, and when I say game of life, I use the word game very carefully about the life people can live beyond the tough problem solving. So when someone is in game mode, and they're optimizing for the icing on the cake versus the cake itself, let's call that portion of life the game of life. I think the final boss stage is the stage of being content, at least from what I observe and what I admire in people. They can be content with lots and they can be content with little, but the state of feeling content and feeling like I have what I have and actually I'm striving for less and eating less, that to me is the based on what I look around and look at is that the final it's a double edged sword you know Constance because yes there is great virtue to be had in contentment but I think also sort of the fundamental challenge of the human spirit is progress forward motion and the trick is always how do you balance that spirit of contentedness with a measure of ambition?
46:16How much is too much? On either side. On either side. For instance, I sit here, I just told you about sort of how I feel my life is today, where in my own personal life, I feel content. But every day, I'm driving these guys nuts about sales numbers every day yeah i'm going crazy every day yelling screaming doing this do this have you do this have you called this customer have you been you know and i sit down you know why do you want a bigger sales number well because this company has to grow and there's so so how do you balance exactly how do you balance that sort of state of personal content and as we wanted to start with maintaining that ambition, right?
47:00And sometimes that ambition is just part of who you are. You can't shake it. So how do you channel it?
47:07The Gstaad Guy:I think you actually answered that a couple of moments ago, a few moments ago when you said you're channeling a lot of that desire for progress in something that's greater than you. And I think that's actually the best channel. where you have loved ones, mentees, and a community of people that you want to bring on a journey of growth. What the driver of that is, I think is secondary, in my opinion. The fact that you're doing it and that you're on that mission, I think is actually the primary, based on the level of passion and heart and everything you've been saying. And what you've been doing, I think the answer is right there.
48:00The Gstaad Guy:Just as a listener. This podcast is brought to you by Pubelle by The Stard Guy, bringing you charms hand-painted with enamel on 925 sterling silver, allowing you to express all the things you love and all the things you might question, from reaver bateaux to backgammon board and caviar tins to paddle rackets. There is a poubelle charm or completed set for everyone in The Know. Thank you so much for watching and enjoy the podcast. May I ask you, are you a father? I have two sons. Two sons. My oldest son is 19. My youngest son is 17. My oldest son is a math major with a minor in computer science.
48:46And my youngest son is in 11th grade in high school. and he's preparing to study some discipline of engineering like his father.
48:58The Gstaad Guy:That's beautiful. Well, your sons, based on everything you're telling me today and everything I understand about you, are growing up among privilege. And I can tell that you won't allow that to define your sons based on the values you hold dear to you. with sons, and this is something that really is a subject that is so dear to my heart. You know, daughters are no less important, but I think that, and you would agree with me, that there's just been sort of this recent, maybe not so recent, but a lot of young boys are lost, looking for direction, you know, based on a lot of the way society has evolved, you know, maybe
49:59prescribing the wrong approaches to a sort of manhood or just not having the right role models or father figures or fathers, period, right? So it's something that I talk about even on my in the early days of instagram i i used to sort of talk about this a lot it's like we have a responsibility to these boys to shape them into men and i would i always sort of like would caution and admonish the guys on whether whatever small groups like you have a responsibility not just to your own sons but to any young man in your sphere of influence you have a responsibility to mold them into a proper man. And so, of course, that starts with your own progeny, no matter how speaking, my sons.
50:56There is an adage that says people work so hard so that their sons can have an easier life. And then they get mad at their sons for having an easier life. It's sort of like that, isn't it? And sort of, you know, you tell them, oh, you're not doing when I was my age, when I was doing this and this, you know. But they don't have to, right? They don't have to. And many ways, necessity is the mother of invention. They're not going to have the life that I had, right? It's just not going to happen. I think the question is, how do you allow them to have the life that they deserve to have without trying to engineer their lives?
51:46I'll give you an example. When my oldest son was applying for college, I said, listen, you're going to Harvard or Yale. Full stop. I'm not hearing anything else. right? You're going to Harvard, you're going to Yale, right? Period. And, um, and he says, oh, dad, but I want to study math and computer science. I'm like, yeah, you can go. I don't care. Go to, you can go to Harvard or Yale and study animal horse boundary, right? You can study, you know, study, you can go there and study animal horse boundary. I'll pay for it. It doesn't matter what you study. You know, the only thing that counts is like Like you said in one of your reels, like, I went to a small college right outside of Boston.
52:34That's all you want. I went to this small college, like, you know, like not the HBS guys. I said, look at me, I went to HBS.
52:47I went to a small college just right outside of a place called Cambridge. Exactly. So I wanted him to be one of those, you know, because I'd seen it. I'd walked on Wall Street. Like I said, I sort of I had a chance to look into the lives of these of the Constances of the world. So, OK, if I wasn't able to be a Constance, my son's are going to be Constances. Right. And I have the playbook. So you're going to follow my playbook because this is the way it's done. Right. So, you know, when it gets the time for them, for you to sort of, you know, sort of run them through that playbook. Sometimes you're going to run into resistance.
53:23Like I did. Like myself, I don't need to go to Harvard. I need to go to Yale. I want to study math and computer science. And there's so many other places that are better at it than Harvard or Yale. Right? Like, are you stupid? Don't you understand that, you know, you get your ticket punched at Harvard or Yale and then you're home free for the... Like, they don't look at life that way. and you can't force them to see things through the prism that in many ways you kind of wish you had somebody to tell you so that you could have gone through that and i think that's one of the biggest dilemmas right when it comes to this idea of providing guidance to your son or sort of to your you know even to people like hashim who's young enough to be my son is where do you draw the line between sort of like gently guiding them and just sort of being entirely sort of, you know, prescriptive?
54:24The Gstaad Guy:Based on everything you're telling me today, Cleveland is such a big part of who you are. And it is such a big part of your grit as a man. You fought so hard in Cleveland to get to New York. You fought so hard in New York to become an entrepreneur. So as a father, when you know the grit is such a big part of who you are, I know you don't want to send your son to Cleveland because you care for him and love for him. But at the same time, I can see that you want your son to share that grit. So how do you prescribe grit without also being unreasonable? Because you also want the privilege, but you want the tools.
55:08The Gstaad Guy:So it's a tough balance. I hate to say this. I hate to sound cynical, but it's not possible. It's not possible. Look, we are products of our own experiences. You cannot engineer. You cannot, what's the word I'm looking for? You cannot artificially engineer an experience, right? They're just not going to be who you are because they don't have those experiences and they have no reason to have those experiences. I think the question I ask myself is how can they do, how can they live a purposeful life in spite of that, right? And, you know, what is grit? grit is not this absolute thing, right? It's a question of degrees.
56:10And, you know, grit is in many ways velocity. How much velocity do you need to overcome a certain measure of resistance, right? So it's not an absolute number. It's all a relative number. And so if they don't have this concrete wall resistance, do they need the same level of grit or degree of greed to sort of power through life? I don't know.
56:35The Gstaad Guy:It's very, very well said. Do you understand where I'm coming from? Of course. You don't need a flamethrower to light a candle. Right, right. If you're lighting candles. Yeah, maybe they don't need a bazooka to blow through this wall, you know, maybe because the wall's been already blown open and all they need to do is walking with a rifle. And with a Harvard degree. Oh, with a Harvard degree. So I don't know. I don't know that there's any way to, you know, either physically or just sort of even mentally to instill that grit. You can teach them values and you don't even teach them. Right. They absorb these values by watching you and seeing who you are.
57:26You can't teach kids anything. You can only transmit who you are and values through your own actions. And so that is really the only thing you can do. Right? You can't control whether they acquire enough grit or whether they acquire enough sort of resilience or what have you. You can only hope that you live your own life in such a way that they're able to see what it means to be a man. and whatever they do with that which they take away. I'll give you an example, Constance. I always say this on my blogs, on my IG, that the greatest gift my father ever gave me, and I say this and I say this with all honesty, the greatest gift my father ever gave me was allowing me to watch him.
58:28And I mean it.
58:33The only reason why we're sitting here today, right, and having this conversation in these circumstances with Consance from start is because it's not because of the material things I inherited from my father because I inherited none. I decided to go my own way, right? But at every step of that journey, I could see him every morning getting up at four in the morning, sitting in his den, in his library, designing, doing this or that, like just the way he lived his life. I still remember to this moment, when you have this sense, when you know where you've come from, it's an invisible, invincible power.
59:23You say, that's my father. Whatever he has, I have it. And it's now left to me to uncover that thing through my own, by dint of my own efforts. But knowing where you came from, knowing that you have that latent potential, right? Right? is incredibly powerful. And more, more, more powerful than any amount of money you can bequeath to your children. I say this 100 % honest to God, hands-on-heart truth. Just that sense of who you are, giving your kids, at least I acquired from my own father, that sense of who I am.
1:00:16i always felt i was this powerful being at every juncture at every juncture of those challenges are sort of like i always knew because i only had to sort of refer back to my father and my grandfather which is another story i come from a lineage of warriors my grandfather was a king and a warrior you know when you have a sense of your own bloodline right and i speak for myself right when you have a sense of your bloodline um and you and you communicate that to your own children like when you when you know where you've come from right it just gives you this supernatural confidence to march into life and really i think that's the only thing you can give to kids you can't force things you can't sort of force these experiences, you can sort of create resilience in them out of nothing.
1:01:11But I think, you know, either through your own actions or the way you live your life or even sort of occasionally pulling them up and telling them stories about where they've come from. You talked about your friend, right, from start, who could have been pulled out from a thousand years ago and could have been a noble count or count or whatever it was, the other thing you said a counter or a duke a duke right it's like do you know why he walks that way do you know why he walks you say he walks with his hips forward and he throws his shoulders back and and he kind of walks like like literally without saying anything you know that this guy comes from pedigree comes from money yeah right it's because he knows he knows where he comes from That's where his confidence comes from.
1:02:04I know where I come from. I come from a long line of warriors. Every challenge I face today, I see as an opportunity for me to earn my place in the ranks of my forefathers and predecessors as a warrior in a new age. Anytime I fall flat is a failure. And a stain on my lineage and heritage as a warrior. That is powerful.
1:02:39More powerful than any amount of money. And that is what I have. That is my gift. That is my superpower.
1:02:53And so if I wish for anything to bequeath. the most valuable thing I can bequeath to my own sons is that sense of who they are. To truly know, absorb and acknowledge who they really are. And if that's all that you've bequeathed to them, I think you've done more than enough.
1:03:19The Gstaad Guy:I want to give the audience the privilege of a quick pep talk from you for the rest of their days today. I know there's a lot that has to be done and a lot that can be done. A few quick tips. Today, they want to be the best versions of themselves and they want to learn something from you. Are there any quick things that the young men listening can think about and look out for to be the greatest version of themselves today? I know what you want me to say, but I think it would be disingenuous for me to say it. You want me to read out a list of prescriptions? Yes. And then clap for myself because I have done all those things and now, you know, you see where it's gotten me?
1:04:21But I think that would be wrong. Be a disservice. I think my own life has shown that there is no prescriptive approach to life. You cannot make someone who wants to do something not do it. And you cannot make someone who doesn't want to do something do it. If somebody wants to do something, they will find a way to do it. If somebody aspires to something, if you're a young man watching this and you truly deep down in your heart aspire to be your highest self, you will find the answers. And those answers are not going to come from me. I'm sorry to say. Because I don't have them. But if my own story is anything to go by, is that there is no prescription.
1:05:24The only thing is desire. You have to desire it. You have to desire an outcome for yourself, for your life. And when you desire an outcome for yourself, for your life, trust me, just like you said, you can learn to do anything on YouTube. You will find a way. You will find a path. You will find the answers.
1:05:57Where did I meet you? Instagram. How did I have half of the people that work for me, or work for Ascogi? Some of these guys, when we were nobody, they showed up every day. I noticed names. I would like notice, because I would go everywhere, like, who is this person that's always here watching the stories, asking questions, contributing? And then I noticed, like, just, you know, like, someday somebody, you're going to get called up to bat. So he wasn't looking for a job, right? But he knew what he wanted to do with his life, which is he wanted to learn, understand what he needed to learn to be the best version of himself, which is to look a certain way and look the part.
1:06:47He wasn't there looking for a job. He was there looking for knowledge. And that knowledge, basically, four years later, has landed him where he is today as a head of design. Could you have scripted that? I couldn't.
1:07:07so in the same way no one could have prescribed that prescribed that part to him you can't prescribe things to people you can only say you have to be clear in your intent and in your desire and if you're clear in your intent and your desire somehow the universe conspires right to introduce all the people you know the constances of the world
1:07:33that are going to be necessary to get you to where you need to be. I'm sorry. I'm sorry, Constance. I'm sorry to burst your bubble or to kind of crush your...
1:07:47The Gstaad Guy:You may think you are, but my intent and my desire was clear. It was to get some sort of direction from you, and that I did. You thought you didn't have the answer, but the answer is clear to me. For those listening today who want to channel the best version of themselves today, know what it is you want to channel and know what it is you want. Know your desires. I could not agree about this more. I think always being aware of the mission that you want to go on and what you want to work towards. and knowing the what and knowing the why and the how will fall into place as long as you're mission obsessed.
1:08:35The Gstaad Guy:I could not agree more. And I think that is all I could ask as a great lesson for all those listening. It's a beautiful thing and it resonates deeply with me. So I got it. There was a will. I got the answer. It's what I was looking for. On this podcast, we always play a game of à la poubelle versus fantastique. And you have shared a lot of fantastiques today. You've shared a lot of things you love and celebrate and that you are grateful for. I'd love a couple more. Can we start with the à la poubelle? What are things you want to throw away and change? Well, it depends on what character am I portraying.
1:09:19Am I portraying prof on social media or okie? I think we've heard of that. If I'm portraying prof on social media, I would say a la poubelle is get rid of the skinny trousers, guys. I agree. Get rid of the skinny trousers, the absolute a la poubelle, absolute trash, right? Or the tan shoes with the navy suits and a number of my other peccadillos out there. But yes, the prof character says, a la poubelle is no more skinny trousers. Let's wear trousers that make us look like men. Wear proper, full-cut, well-draped trousers.
1:09:59The Gstaad Guy:I agree with that. And better still if you get them from Ask Hoki. There we go. There we go. What about an a la poubelle? In my personal life. In your personal life. A la poubelle in my personal life, without turning this into a long story i'll give you a short version of it right and it's not so much a la pubera as what not to do or what i found to be not helpful we come up in this life and even the great old book said that alexander modeled himself after you know alexander great modeled himself after his teacher Plato, Aristotle, and so on and so forth. And Aristotle modeled himself after Socrates, who was his teacher.
1:10:49So it's always important to have a model, right? To model like your father, like my father, right? But I found that where I went wrong once in life, and it was a very difficult lesson for me to learn because I had spent too much time on the wrong track. When I was a young banker, there was an African-American businessman. His name was Reginald Francis Lewis. Very successful in the 80s during the LBOs, right? You know, he went to Harvard Law School, came out, worked for Paul Weiss, became a Wall Street lawyer, did LBOs, had a chartered jet, had his own private plane. When I came to Wall Street, you couldn't tell me anything.
1:11:34This is all I wanted. I wanted to just copy and duplicate this guy's life. This is going to be me. I read this biography cover to cover. I have it highlighted, yes or no? Have it highlighted in yellow highlighter with red markers. I literally sort of copied, like literally, like even the cigars I smoke, right? It's because of this guy. I was so intent on being him that I was going to make myself. I was going to force, like I was literally going to physically force myself to manifest being the next Reg Lewis. But it failed. It failed because, not because of the lack of effort, right? So I tried to do certain things, sort of, I tried some of the businesses, sort of, ideas that made him super successful.
1:12:31And I was never that successful. doing that. Not anywhere close to how successful I've been being myself. So I learned a bitter lesson. You might call it a lapu-bel, was that so many times we spend our lives trying to be somebody else. Where our true fortune lies? in being simply who we are. It's really so simple, it's stupid.
1:13:12Do you understand what I'm saying? Tried so many years being somebody else. Frustrated. Money burned. Failures. Knocking against the wall. You know, wondering why, you know, and then, the moment you say I'm just going to be myself right on a whatsapp to five people I'm just going to be myself to five people on a whatsapp group becomes three million people today by doing nothing else other than being yourself it's cool do you understand what I'm saying
1:13:54The Gstaad Guy:yeah I do and something you can relate to, of course.
1:14:01So I think that's what I would consider. It's a very long, it's not so much à la poubelle or what I wouldn't do if I knew any better and what I hope somebody would avoid. It would save them a whole lot of time and heartbreak.
1:14:19The Gstaad Guy:That's very useful. I appreciate that. Fantastic.
1:14:27I think fantastic on a personal level, right? So let's forget the Prof. Avada for now. Fantastic is, I don't know if it's as fantastic as it's sort of my own, what I've discovered is that whatever you define as your ultimate destination, your goal, this thing that you aspire to, understand that it's going to cost you and that there will be one day when you'll be sitting alone and have those things and ask yourself was it worth it it doesn't matter how good you have it it doesn't matter i don't care if you've sort of like you know been able to do you know kind of reinvent the moon, right? Because the sacrifices you have to make to get there are in direct proportion, almost to the degree of whatever it is you're looking for.
1:15:32I guarantee you, I bet you, there will be when you get there, if and when, I hope everybody gets there, where you're going to sit down and ask yourself, really, was it worth it? Many days, the answer is, I don't know. And for me, that's a fantastic thing to know that every person will confront, no matter the degree of your success. And I think most people, if they are true to themselves, will say, I don't know.
1:16:06The Gstaad Guy:It's a cool question to ask yourself. I think a lot of people who have a strong desire to achieve and have not embarked on that journey yet dream to ask themselves the question, was this all worth it?
1:16:26The Gstaad Guy:Different questions for different phases of life, I think. But it's a true and deep question.
1:16:35The Gstaad Guy:I really appreciate you, Prof. Okie, for being so open today, for speaking of things that are not easy to speak about, for opening up and for allowing us to learn more about you, to learn from your story and have this conversation. I really enjoyed sharing this couch with you and I'm sure the audience listening share a lot of that feeling with me.
1:17:09The Gstaad Guy:Likewise. Likewise, Constance.
1:17:40The Gstaad Guy:First step, new denim. Abercrombie added new linen blend jeans to their lineup. They're really lightweight and a comfortable cotton linen blend you need for summer. Their archived shirt is your next must-have. Cut it a 90s-inspired oversized fit that gives a put-together but relaxed look. Pair it with their classic poplin short and you have your new go-to outfit for the season. Set your wardrobe up with Abercrombie this summer. Shop in the app, online, and in stores.
From the publisher
The Gstaad Guy sits down with PROFF, the man behind the AskOkey universe, a former JP Morgan investment banker turned tailor, blogger, and one of the most quietly compelling voices in men's style, to explore what it truly means to dress with intention and live with purpose. From the boardroom to the cutting table, PROFF reflects on a life shaped by reinvention, resilience, and the profound relationship between how we dress and how we carry ourselves.
The conversation ventures into the philosophy beneath the cloth: the stoicism that steadies him, the desire to grow that drives him, and the responsibilities inherited along the way that forced him to find his footing faster than most. PROFF shares what it means to build something from nothing, why necessity has always been his greatest teacher, and how observation, solitude, and a commitment to becoming the best version of yourself can quietly transform a life. A thoughtful and deeply personal conversation about identity, grit, and the elegance of knowing exactly who you are.
Filmed in the One&Only One Za’abeel Royal Suite.
(00:00) Intro ✨🎙️
(00:58) Aura ✨🌀
(02:55) Solaro Suit 👔🌞
(05:32) Ask Okey Universe 🌍🙏🏼🙏
(07:49) Public Persona 🎭😎
(09:55) Becoming A Tailor 🧵✂️
(11:58) Audience Engagement 🎤👥
(15:04) What You Stand For 🏛️💪🏻
(17:00) Life Changing Moment ⚡🔄
(20:00) JP Morgan 🏦💰
(26:30) Playbook For Life 📖🗺️
(28:27) Stoicism 🧘⚖️
(30:18) Desire To Grow 🌱📈
(34:18) "Why Am I Doing This?" 🤔💭
(37:40) Spending Time Alone 🌙🚶
(38:49) "The Journey vs. The Destination" 🛤️🏁
(40:49) The Irony Of Life 😏🔄
(43:46) Being Content With Progress 😌✅
(47:35) Family 👨👩👧👦❤️
(48:39) Necessity Is The Mother Of Invention 💡🔧
(53:00) Gentle Guidance 🧭🌿
(53:26) Grit 💪🏻🔥
(57:25) The Greatest Gift Is Observation 👁️🎁
(59:56) Knowing Where You Come From 🌍🏠
(1:02:21) Be The Best Version Of Yourself 🌟💯
(1:05:38) Looking For Knowledge 📚🔍
(1:08:01) À La Poubelle vs. Fantastique 🗑️✨
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