Hi, this is Dan Morrell, host of Skydeck.

Byron Wien (MBA 1956) was a Wall Street icon. He had a 50-year career that included chief investment strategist roles at Morgan Stanley and Blackstone, and was well known for publishing an annual list of the “10 Surprises” that investors should be thinking about in the year ahead.

Taylor Becker (MBA 2025) met Wien as a first-year analyst at Blackstone, the only one of the 100 or so in his cohort to take Wien up on his offer for a 1-on-1. That first meeting led to a mentorship—which in turn led to a memoir of Wien, Stay at Risk and Live Forever: Lessons from a Life of Curiosity, Grit, and Reinvention, which was co-authored by Becker and released in November of last year—a little over a year after Wien’s passing.

In this episode of Skydeck, I talk to Becker about the forces that forged this legendary character, the 20 hard-won life lessons he loved to share, and how even this icon suffered from imposter syndrome.

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Dan Morrell: There was an initial fascination, obviously, that attracted you to even go and meet with him, right? And then you’re on his team and that continues to be there and continues to grow in some way.

So at some point you decide this man is a story. And it's a story that I want to tell. What convinced you of that?

Taylor Becker: Well, I mean, this was definitely something that happened organically over time through working with him—at this point probably three or four years into it. Just hearing him tell these stories, whether it would be in client meetings or over a meal, you would hear just the craziest stories about fed chairs and, you know, politicians, and just titans of industry. He had co-authored, George Soros’s book, Soros on Soros, and he’s very close with him. He hosted these “Benchmark Lunches” in the Hamptons every summer for I think thirty-some odd years, and it would be twenty to thirty people at every lunch, maybe a hundred over the course of the summer.

And it would be every tech, finance, business titan you can think of. And so hearing all of these stories over the years, I would always hear people say, Byron, you have to write these stories down.

Like, if we’re just hearing one nugget every now and then, how much treasure is there that’s going unearthed? And, he would always just wave his hand dismissively and grumble—there are too many books in the world, no one wants to read a book about me. That was kind of characteristic of him, is … some of it was maybe a false modesty, but a lot of it was very real.

So, fast forward to the summer of 2020, the pandemic hits, we’re all working from home. He was complaining about not being able to go into the office every day. We would be on Zoom and I’m like, I don’t feel that bad for you.

I can see your, you know, lake in the background of your house in the Hamptons. I’m sitting in my shoebox apartment in New York. But I did have this idea that kind of clicked. I was like, Byron, let’s put an hour a week on the calendar. We’ll just chat. I'd love to learn from you. We’d been working together a long time. He was already a mentor and a friend, but we didn't have this structured time. And I said, I’m just gonna ask you questions. And I’m gonna write down your answers if that’s alright.

He's like, okay. And we did that for a number of months. And at some point, I realized I had tens of thousands of words that I had written down. And I sent it to him, kind of packaged it up and sent it to him. Didn’t call it anything, but I was like, Byron, this is starting to look a little bit like a book.

And he was like, ugh. I kind of, I kind of ensnared him in that way.

DM: Was he happy with it by the end?

TB: By the end he was. So we worked together on the book starting that summer. We didn’t officially start calling it what it was for maybe, call it, six months or so. And then we worked on it together iteratively until I left Blackstone in August 2023.

At that point, we basically had the draft finished. He reached out to a few publishers. We got interest from a couple. And then he unfortunately passed in October 2023, right after I enrolled here at Harvard Business School. And a few months went by and I connected with his wife, Anita, and I said would you support if I reached back out to those publishers to see if they’re still interested even though the big guy is gone.

So with her support one of the publishers was still interested and we moved forward with it.

DM: The book is filled with lessons, right? You know, it’s his life and he turns his life into all these lessons, all this actionable intelligence that you can pass down. And I want to talk about one of them specifically. He says, when you meet someone for the first time, treat that person as a friend. Essentially, assume good intentions. And that feels so at odds, I think, with the expectations one might have for a Wall Street operator, right? Is this optimism about humanity a rare quality in the industry, or have I just watched too many movies?

TB: Yeah, I think part of this is definitely unique to Byron. You definitely won’t see everyone acting like that, certainly not in high finance. People can be very pragmatic, very utilitarian about their relationships. A lot of that is just a matter of time and the amount of energy you’re able to exert really connecting with people.

It’s obviously a very stressful, high stakes, fast-paced environment. To him, I do think there was some element of it that was useful for him. He was huge into networking. He was a prolific networker and I think he realized, over time, you will be much more successful in your networking and much more successful in your relationships with people if you start out assuming good intent and goodwill. I do think there was that element, but I think he also just had this belief and understanding that if you treat people as a friend, they will like you, they will trust you. But he did acknowledge that if you trust people and treat them as a friend from the beginning, you will get burned. And he got burned a few times, including someone who was very close to him when he was, you know, kind of middle aged, and he was never really able to let that go and it stuck with him, but it didn’t change his outlook and he didn’t become bitter.

He kept going anyway, and I think that is rare.

DM: You know, there's like a time stamp on a lot of his revelations about life, and, and he had that revelation in his 40s, and a lot of them came in his 40s, and I want to read another one, another one of his maxims.

He says, “Most people don’t become comfortable with who they are until they’re in their 40s. By that time, they can underplay their achievements and become a nicer, more likable person. Try to get to that point as soon as you can.” What do you think your classmates, who are just about to enter the workforce, can learn from that?

TB: Yeah, I love that one. I think if you think about some of the most successful people in the world, if you think about the tech titans of today, they are by no means very humble people.

And I think there’s kind of this idea that the more successful you are by and large, the more you have to talk about yourself, the more accomplishments, the more stuff you can tout and be proud of and tell people about, and that’s true. But what I found and I think is relevant to my fellow classmates here at HBS and future students, some of my favorite people, and by and large, the people who I connect with at first, are people who don’t lead with their successes.

Obviously, when you’re quite young, you’re writing college essays for yourself and you need to tout the amazing things about yourself. This is necessary when you’re younger and don’t really have anyone to vouch for you, frankly. But when you do start to accumulate some of these things, to try and reach that point of security as soon as you can, basically, Byron says.

It makes you way more likable, and I think generally will also make you approach relationships in just a much less self centered and kind of utilitarian way.

DM: I want to talk about something also that you wrote in the preface, and it’s that at some point, Byron talked about how he felt like he suffered from imposter syndrome, which is so surprising for this icon of Wall Street. How did you reflect on that? How did hearing that from him impact you?

TB: Yeah, actually, that story… his wife even didn’t know about it until she read it in the book, and she was surprised by it, too. I think it surprises almost anyone. It certainly surprised me. Everything that he published, he was one of the most widely read analysts on Wall Street, always on TV, and he did exude this confidence.

Some of that is necessary, if you want people to take what you’re saying seriously, especially if you’re telling them how to invest their money. But, I think he taught me this very key thing, which is that no matter how much you achieve in life, there will always be an element of wondering how much of that was luck, how much of that was serendipity, how much of that was because someone kind of put their thumb on the scale to give me a recommendation or kind of help me get my foot in the door.

Not everyone has this kind of nagging inside of wondering how much that is true. I’m kind of scared of those people. I think everyone who is humble and recognizes how much of life and success actually is being in the right place at the right time. Obviously working hard, making good relationships, and all that. But that was so impactful for me, not just because it taught me something about myself and becoming comfortable with that imposter syndrome—and becoming comfortable with the idea that it maybe never goes fully away. But it also helped me respect him so much more that, as a mentor, he was willing to be vulnerable with me and open himself up to me in that way.

I think we should all aspire to be mentors like that in our lives.

DM: I know I’ve read you a lot of quotes from the book, and I've read you a lot of the life lessons, but this one is actually my favorite, so I want to read this, and it’s my favorite quote from Byron. He says, “Never retire. If you work forever, you can live forever. I know there is abundant biological evidence against this theory, but I’m going with it anyway.” I feel like you can get a sense of who he is from that quote, but what do you think drove him? What did he have internally that pushed him?

TB: Yeah, I mean, that quote, it really inspired the name of the book.

Stay at Risk and Live Forever. Obviously, lots of biological evidence against that. Byron’s no longer with us. So for him, “never retire” did literally mean he worked until the day he died and was actively contributing. But for anyone what it means is don’t give up on that thing where you’re constantly trying to learn and putting yourself out there in a way that does put you at risk in some way.

It might be the risk of embarrassing yourself in some way. It might be the risk of some athletic endeavor that really scares you, but that's really what drove him to the end. And another thing he always said, “Why would I retire? Everything I’m doing in my job, I’d be doing anyway.” And I truly believe that at the age of 85, he would wake up at 6 a.m., and the first thing he would do is go to his Bloomberg terminal and pull open the physical copy of the Wall Street Journal and New York Times, like he did every day, that he read cover to cover. He’s like, if I can get paid for that, and I'd be doing it anyway, awesome. And that’s another kind of takeaway, is if you can find that thing that you love, and you can get paid for it.

Then you won’t want to retire, at least not all the way, and I think that's inspiring.

DM: You had this remarkable opportunity and a remarkable experience to sit with Byron and then write this book, right? How do you think this experience changed your perspective and perhaps your trajectory?

TB: I mean, starting out from college in a job like this, finance—and especially where I worked—can be very hierarchical and there is kind of a known formula for the way a young person acts and the way that they add value.

It typically does not look like coming up with ideas and sharing them and then also pushing back on the ideas of people who are 30 years your senior, let alone 60, 70 years your senior in my case. And something that was so formative for me was when he saw me at the time 23, 24 years old, and he’d be like, well, what do you think?

And I’d be like, I don't know what I think and I’d come up with something. But getting used to actually raising my hands and expressing that. And then also, he would be, he would say something, he would have an idea, or a concept that he was talking about, and he would ask, So, do you agree? Like, do you disagree?

And you would expect me to push back. I’ve always been a relatively opinionated person, so I think it came a little more naturally to me than other people. But, that’s something I learned from him, is that good ideas can come from anyone.

And in terms of writing the book, some of this continued. I will say, he was not the easiest person to write a book with. He was quite opinionated himself and he was constantly evolving and like changing his views, but he also was in his late 80s and had a set way of doing things and was not always the most flexible in certain ways.

This was a challenge that I learned to mitigate. But I think one of the core things that I learned practically that I think is good for anyone is to really take the time, spend the time, recognize the value in, and take the time to talk to people who are way older and way wiser than you. I think it’s something my generation really doesn't do a lot. And when we’re here at Harvard Business School, so much of it is studying history.

The case method is essentially, studying what’s happened in the past and trying to apply, you know, to the future today. And it's a skill set that we are picking up, and we're doing it in a classroom setting. I think we should be doing it in our personal lives a lot more than we do. Take the time, propose an hour meeting with someone regularly, if they’re a mentor, and they’re willing to do it.

DM: Taylor, what is the advice that Byron has in this book that you think is most relevant to your HBS classmates?

TB: One of his life lessons was, “When seeking a career as you come out of school, always take the job that looks like it will be the most enjoyable.

If it pays the most, you’re lucky. If it doesn’t, take it anyway. I took a severe pay cut to take each of the two best jobs I’ve ever had, and they both turned out to be exceptionally rewarding financially.” And a couple of the life lessons are about jobs.

But this one in particular, I think, there’s such an expectation—there was when I was at Penn, and getting your first job out of college there is here as well—[that] you don't want to make below the median salary. We know what we can make in a lot of different jobs. And I think a lot of us have this expectation: Well, I’m gonna get that consulting job or that finance job out of HBS, do it for a couple years, then I’ll figure out what I want to do. Like yeah that startup job I got an offer, but it pays this much less than the other one. I think he had this view that if you pick the job that you actually think is most interesting you’re going to perform at the best of your ability. And if you’re working with good people and you’re adding value, working hard, the money comes. Careers are long—certainly in Byron’s case careers can be very, very long and the money comes, but I think something important to keep in mind and to not make short-term decisions and of course, everyone’s circumstances are different.

Some people have student loans to pay off like that. Not, you know, not everyone's in the same position, but if you're in a position where you can make that harder choice, Byron at least would say that it’s always worth it in the end.

DM: Taylor, how did you hear about his passing, and how did you reflect on that in the moment?

TB: Yeah, so, I had only been at Harvard for a couple months. I actually spoke with him very regularly. We were very good friends at this point.

And he would also love to call and hear about how school was going, especially because, you know, he went here in 1956. That was 70 years, you know, gap in time, just about—60 some-odd years. And he would love to hear, do they still do this? Are you still writing everything by hand? And he was very disappointed to learn [about] all the technology that we’re doing now.

But, you know, I was also very close to our assistant Maria at Blackstone. And she started texting me about a week before he ended up passing, saying he’s not doing well. I was a little prepared, but also Byron had had health scares in the past, which is not unusual for someone in their 80s. He had always bounced back, including when the doctors would say, you know, he probably doesn’t have much time.

He’d bounce right back and go straight back into the office the next week.

So I kind of had this built up—uh, part of it was selfish hope that it was all gonna be okay, but part of it was also pattern recognition.

DM: Mm hmm.

TB: This time I got the call that he had passed, and I remember I was in Shad, and I stepped outside.

I was sitting on a bench, and yeah, I think it was obviously a huge loss in a lot of different ways, but one of the biggest things is that he was always in my corner. He encouraged me to go here. He encouraged me to leave. He said, I would hate for you to leave Blackstone, but if we’re not creating the opportunity for you to stay, I’m going to help you find the right thing, which is so rare for a boss.

And I had this realization that I don’t have that person who I can always call with the exact perfect advice. In a way, it’s like, I’m kind of on my own now. Obviously, I have my family and they're amazing, but I’m the first in my family to go to college. A lot of the things that I do, my parents have great wisdom, personally, but have no experience in a lot of these things.

So that was obviously personally hard, but also prompted me to be like, Okay, I actually do have to start figuring out a lot of this on my own now. And develop tools and new relationships to kind of figure it out along the way.

Skydeck is the Harvard Business School alumni podcast featuring interviews and insights from across the world of business. It’s produced by the External Relations Department at HBS. Our audio engineer is Craig McDonald.

It is available on Apple, Spotify, and wherever you get your favorite podcasts. And if you could take a moment to rate and review us, we’d be grateful.

For more information, or to find archived episodes, visit alumni.hbs.edu/skydeck.

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