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Episode 6: Redefining Success With Ian Winer

Richard Janes Podcast

Have your parents ever tried to live vicariously through you?  For my guest in today’s podcast, that was what most of his early-life was controlled by: another person’s desires. From a young age, all his father wanted was for him to be a star Ice Hockey player. Nothing was more important. After a lost childhood chasing his fathers dream, Ian was accepted to WestPoint (where again he played Ice Hockey, captaining the Army’s team much to his father’s satisfaction). But, after a machine gun accident in South Korea Ian finally made his way to Wall Street.

Today, Ian Winer is an investment expert and a frequent contributor on CNN Money, Fox Business, BBC, The Wall Street Journal, and The Financial Times.  But here’s the thing, until recently he wasn’t sure what his Passion & Purpose was. His life was still being led by what others said he should doing. Until one morning, when he hit the send button to his entire email list announcing that he was leaving Wall Street and going on a quest to connect with as many people as possible.

Learn how Ian was able to reclaim his identity and take one big courageous step towards finding his unique passion and purpose.

In this exciting conversation we talk about:

  • How Ian redefined success for himself
  • How to take your skills and turn them into success
  • How to maintain your core-self during times of change
  • What holds people back from embracing their passions
  • How to get out of your own way and embrace the fear of change

Ian’s story can inspire us all to ask “Why?” in our daily lives and teach us that we each have our own, unique purpose.


  • What stopped you from making changes to step into your best self?
  • How has human connection impacted your success?




I’d love to hear your thoughts on this episode. Who was your inspiration for following Passion & Purpose?

For full disclosure, Ian Winer was a student in my Personal Brand Masters Program.



Thanks so much for listening!

Click To Read The Full Podcast Transcript
Richard Janes: If you live and breathe investments, you’d probably recognize the voice of today’s guest as he’s a regular contributor on CNBC, CNNMoney, Fox Business, Bloomberg, the BBC, Wall Street Journal, The Financial Times, Business News Network… well, you get the idea. And if you need an expert to talk about the state of the markets, he’s your man. Or at least he was until May 15th when at 3:15 AM he hit the ‘send’ button on an email to his entire contact list.

As the financial community got to their desk that morning, they read in shock.

“So long, farewell Auf Wiedersehen, adieu.

Friends, after 22 years and a significant amount of mileage, I’ve decided to leave Wall Street.

I’ve reached that crossover point where whatever income I’m leaving on the table is less than the opportunity cost of missing out on life.

As many of you know, I’ve written a book based on my philosophy designed to connect people to each other. It is due to be published in 2019.

Writing a book and living the message are two very different things. It is time to walk the walk now.

In August, my wife and I will begin our next journey by volunteering around the world for a year and doing our best to be of service. I hope to chronicle that adventure in a second book and on social media. After that, well, who knows.

I wanted to thank everyone for all of the help along the way. You’re my clients, coworkers, but most importantly, you are my friends. I hope very much that we stay in contact as I owe a great deal of gratitude to you.

I will continue to send out an email with a slightly different take on the world but staying consistent with my core values of integrity, connection and fun. God bless all of you and good luck in everything you do. Signing off, Ian S. Winer.”

Richard Janes Commentary: The responses quickly came flooding in.

“Are you really doing this?”

“I wish I could do that.”

“Have you gone mad?”

“Are you terminally ill?”

In the 1950s the Indian philosopher Jiddu Krishnamurti coined the phrase “It’s no measure of health to be well-adjusted to a profoundly sick society.” And in today’s podcast we talk with one man who decided to remove himself from the sick society he found himself in—a society that he long strived to be the best in. If you’d ask him his passion and purpose a number of years ago, it may well have been to make as much money as possible, or, to be the last man standing. And as with many of us, this mentality was developed at a young age.

We’ve all seen those parents who live vicariously through their children, parents whose unfulfilled passion and purpose are impressed upon their mini-me at such a young age that the child can’t fight back. The child has no hope of discovering their own unique identity, their own unique passion and purpose—that passion and purpose that will eventually mark them out as unique and different from everyone else.

Today’s guest is an extreme case and only recently did he take that big bold step to reclaiming his identity and kicking the conformity that had to the outside world, giving him much, much success but internally left him pining for more from life.

Ian Winer: When your father decides that he is going to basically live through you and you’re the oldest, it creates a very difficult relationship because his moods towards me were 100 percent correlated with how I played in a nice hockey game. And so for the games that I played well, there were rewards; for the games that I did not play well, there were pretty severe punishment.

And so, when you’re 5, 6, 7 years old and you’re living in fear because you know that if you don’t play a good hockey game, there’s going to be a pretty severe cost. It’s no longer fun. It’s really a question of survival. There were fun moments, there were moments of certain glory and victory and winning trophies and things that certainly fed good memories in my ego.

But all in all I would say that I missed out on quite a bit because of that singular focus on a sport, and I think a lot of kids still to this day suffer from singular focus on one thing in their childhood. You know, it could lead to long-lasting effects which, you know, still to this day I suffer from certain ailments because sports for me was truly kill or be killed, and that’s why after college, ice hockey I could have kept playing but I decided that I had had enough and I was exhausted of it, and I think that that happens to a lot of kids.

Richard Janes Commentary: How many of us were forced into doing something because our parents wanted us to do it? This could have been through insisting we sit down and play the piano when we absolutely hated the piano. Or the more subtle guilt trip of taking that subject or studying at school that never quite felt right.

Parents want the best for their children, of course they do. And in most parents, that’s a natural wish. But for so many parents they forget that this little mini-me isn’t a carbon copy of themselves, that this mini-me won’t hit the same hurdles that they once faced in life, and that this little person that they love so very much really needs to go on their own journey to discover who they are and what makes their heart sing. It’s such a fine line between providing support and dictating direction.

As a parent of two children myself, one of the most important things my wife and I agreed was paramount to our parenting style whilst that it was our #1 duty after ensuring the human needs of food, shelter and love are met to give our children as many experiences as possible so that they could find their own passion and purpose. It’s tough not to second guess, not to guide them to think what we think is best, but they need to find out for themselves; otherwise, they’ll end up moving further and further away from their own truth and learning to live with a mask that they had no hand in choosing.

For Ian, he lost his childhood through living out someone else’s passion and purpose. Learning that the only way he can survive is to figuratively “kill or be killed.” And given that this was all he knew, it’s easy to connect the dots as to why he would decide to trade the figurative for the literal, and signed up to West Point.

Ian Winer: You know West Point is the United States Military Academy. It is essentially our training ground to make officers in the United States Army. And given my childhood, given the intensity and the yelling and the screaming and all the stuff that took place, West Point was just a logical fit for me. You know, all of a sudden people are screaming and yelling at each other. And you’re just kind of looking around and not really sure what’s happening and you’re quickly learning and you don’t speak unless spoken to, you’re only allowed to say a few things when spoken to.

But within that first day, they weed out quite a bit of people, and people pretty much quit on the spot when they see what is happening. And it just goes to show that you can come into a place like that president of your class or Eagle scout or captain of the hockey team or whatever it is that you were, and nobody cares. And by the end of the day, you’re marching as part of a unit in the exact same uniform with the exact same haircut and outside of your last name on the front of your clothing there is no difference between you and anybody else, and so it’s a huge shock to the system especially for people who have big egos and I was certainly one of them. It is designed to break down the individual and force you to become part of a unit.

No matter how important one thinks that they are, the overall mission is much more important. And it was designed that way. It was designed so that people didn’t think in the midst of combat or in the midst of a mission that somehow their personal wishes or their personal desires somehow were more important than the overall mission of the group. So there wasn’t much sort of room for “Hey, look at me and look at all the great things I can do.” It’s really more about “Well, did the mission succeed or not?” because no matter how great you are, if the mission failed it really doesn’t matter. And so from the first moment you step on to a West Point post or campus, you’re treated like one of many as opposed to just yourself, and that’s a big shock for a lot of people.

Now, I personally found my way into West Point because they were Division I Ice Hockey and that was a must for me, it was free. And when I went to check it out, I had saw a bunch of people running around in camouflage fatigues and everybody was in great shape and everybody seems pretty tough and I thought “Wow, this is the perfect place for me,” as far as excitement, you know, kill or be killed, macho, mostly masculine-type environment and it was the opportunity to play Division I Ice Hockey against some of the best players in the country and so for me, that’s how it all kind of coalesced and led me to my time at West Point.

And when I was Captain of the hockey team, for the first time in years, I took our last names off the back of our jerseys, and it created quite a stir because nobody knew who anybody was out on the ice. None of the fans did. But that was exactly what I thought was the way it should be. And that the name on the front of the jersey which was Army was way more important than any individual person out there, and so, that mentality I think is what that place is all about and I think that that is why that many people that come out of there tend to have success because they understand that concept over the long term as opposed to just thinking about how they can their name in lights.

You truly have a purpose that isn’t related to money. It isn’t related to what people define as success. And when that happens, you can actually be part of a unit where people are truly selfless with each other, that people truly care for each other in a way that just isn’t possible, at least from what I’ve seen in corporate America.

And so when people are not motivated by money and motivated solely by the person next to them; and the cause, the patriotism or, you know, love of country or whatever it is, that becomes greater than yourself and you can feel that. No matter how much I tried to impart West Point-type thinking in corporate America, it just did not work and I don’t think it ever really worked.

Richard Janes Commentary: Now, if you’ve ever been to one of my seminars, you may have heard me say that there are three places that we must conform in order to survive: high school, prison, and the military. The ramifications for standing out in these worlds can be devastating. Through conformity the group is able to be controlled and in tough environments the individual has a better chance of survival when it blends in with the bigger group. But in order to conform, we have to suppress our individuality. We trade our unique passion and purpose for a collective mission, vision and value system that ensures our basic needs are provided for.

But it’s a two-way street. Both the community and the individual are getting something in return; that is, until they’re not. And in Ian’s last year at West Point, while training in Korea, an accident with an M16 machine gun blew out his eardrum and suddenly the community couldn’t make use of him. His career in the army was cut short. And after a few phone calls, he found himself on Wall Street, the heart of corporate America—but still adopting the mentality of the US Army, the ice hockey and his father.

Ian Winer: Wall Street brings out the best and the worst in people and I think it’s like many other careers, there are highs and there are lows. I think on Wall Street those are exaggerated. I had always believed, and much of this was in the military, that there really had to be a big difference in chasm between the leader and the people in the unit, and the reason was because if you got too close to the people you were managing, you wouldn’t be able to manage them. And so, I took that to new levels. I would constantly try to avoid getting close to the people that worked for me, I half-jokingly but half-seriously told them, you know, “Don’t put pictures of your family on the desk because if I got to fire you tomorrow, it’s just going to make it that much more difficult for me.”

And so, I took the mission to a new level and was willing to do anything if I thought it ultimately could help us take the hill so to speak. And what I realized and what happened was not only was that not working, it really wasn’t who I was. It was an act. It was my way of saying like ruling by fear and that I felt that fear was truly a way to kind of keep people in line because when everybody’s motivated by money there is no really esprit de corps, and so it was like “Okay, so how do I keep people at bay and referee all the people that are under me here in the Wall Street trading desk?” It was just like “Well, I got to keep them afraid.”

It was all part of that means to an end. It was all part of that if I have to fire people, I’ll fire; that there are casualties in every battle but as long as we get to the golden line or the hill or whatever it is, it’s worth it. And as time changed and I changed, what I realized was, this is not who I am. I’m a different person. And this act as a manager isn’t working. And then as I became closer to people that worked for me and got to know them and invited them to my house, I realized that I was much more effective but I also realized that I didn’t want to do it anymore.

So I think that it was a moment of consciousness where I went from this sort of voice in my head as to “This is how it’s supposed to be” to my own will and the ability to decide like no, I think that this is not who I am. It’s not a means to an end and I’m going to start acting like who I am outside the office, inside the office. And it made it a lot more difficult to fire people, it made it more difficult to do things because I truly considered these people my friends and it made it a lot more difficult to make decisions that I didn’t necessarily believe in.

Richard Janes: It’s interesting because through the Personal Brand Masters work, one of the things we identified that was always present in any of your success was this word ‘connection’, and yet, there’s been this pattern through your management style of not connecting.

Ian Winer: Yes. And I think that ultimately that played out to a point where I couldn’t make that bargain anymore, and the bargain was, you pay me a lot of money and I’ll run this place like a military base and I will do whatever it takes for us to make our goals, you know, as far as profit and loss and revenue projections. Whatever it takes.

But I was missing that connection. I was missing that connection to people that worked for me. Almost every relationship I had in my life was being affected by these judgments and biases, and so I tried to think about what I could do differently to enable these relationships to move forward. Not necessarily improve but move forward. You know, who they were, why they were. And I began to get more and more interested in that and the goals of whatever they were for the ultimate corporation started to fade away and it became more important as to how I could protect my people and do the right thing for the people working for me. That was, you know, the profound change I think that too place.

Richard Janes Commentary: This would play out that Ian 3-4 years ago would have thought when you start connecting more with people, your profit and revenue is going to go down. What happened?

Ian Winer: They actually improved my last year as managing the group, was our best year in probably all 5 years that I had been at the last firm I was at, and that was, you know, pretty telling. My personal numbers improved and really, you know, you look back and you think, “Oh, why I didn’t do this earlier?” But you start to understand that people don’t all respond to that kind of leadership style and that ability to adapt my leadership style was always a challenge and I was finally able to adapt it and in doing so, you know, opened up my eyes to a lot of different things and realized, ultimately, it’s not what I wanted to do.

Richard Janes Commentary: I had the good fortune to meet Ian when he became a client of my Personal Brand Masters Program, a course where we dig deep to get at the core of a person’s unique goal, enabling them to double down where they can attract more opportunities to really shine and impact both their own life and the lives of those in the wider community.

Now, as we dove into Ian’s history, the word that defined his success, those moments where greatness shone down on him, was connection. And yet throughout his life, he had been pushed into environments where connection was subservient to the overall mission. But just as the sun will melt the ice, larger and larger cracks began to appear in Ian’s day-to-day life, cracks where he started to question the conditioning he had received around his true purpose.

Ian Winer: As scared as I was of leaving my job, it was more frightening for me to see myself in that seat 10 years from now. For many, many years, for most of my life I had an image of success that’s, you know, “Did I go to a good school? Yes.” “Do I make a decent living? Yes.” “What’s the title on my business card? My car, my house?” Where do my kids go to a school?” All those things, people would look at from the outside in and say “Wow, what a success!”

You know, I had equated that financial stability with happiness and so for me, walking away from that at times seemed crazy and the reality is, in the moments where I had the most stuff, my life, you know, personal life was as unsuccessful as it probably could be. And I think over the last year or so what I realized was that definition of success just wasn’t working for me anymore and what I realized was that for me, success is purpose. It’s how can I take the skills that I have, what I have to offer, those core attributes and get into service and actually selflessly try to do something even though it scares the heck out of me in some ways, but to go and do that and confront that fear, to get out of my comfort zone, and to try to actually connect with other people.

If I’m truly going to connect with more people, I truly need to go out and expand my universe and get out of my comfort zone, meet people and learn, and really accept the fact that I don’t know anything for the most part about what’s going on in the world. And if I can admit that and then try to learn, I have an actual shot of connecting with more people. And so that was the journey and it was incredibly personal, it was a journey, you know, with my parents, with many relationships that I had that I felt were unfinished and had things that have been left unsaid, and it was an ability to get closure around a lot of that stuff, and it changed my life.

Now the most important question and the one that is really part of my life is “Why?” And that is enormous change for me. I never used to ask why. I never needed to ask why. I just sort of saluted and executed on whatever the order was. And now, as I approach people and try to connect with them, I constantly find myself asking why. “Okay, you disagree with me on an issue. Why?” as opposed to just dismissing you. You know, why.

So this was happening in the world. You know, why. And the only way that I’m really going to be able to connect with more people is to ask that question and to actually learn why somebody thinks something. Or what happened in their lives so that this is why they’ve come out and feel this way about something. And that, to me, that purpose, that metamorphosis, I think, you know, each person as life goes on thinks about things differently and for me it was really that definition of success changed quite a bit, and now for me, success is, you know, am I happy today?

And it has been a dramatic change from everything from sleeping, you know, 9 hours a night as opposed to 5 ½ or, to being spontaneous, going to movies at 7:00 at night, exercising at 7:00 at night, having dinner on a Sunday night with friends. All of these I’ve done in the last 2 weeks that were not even possibilities for the last 5 ½ years. And so to get that ability to now see how life can be when you’re not getting up at 3:00 in the morning and when you’re not going to sleep at 8:00 at night because you’re exhausted, it’s amazing how enjoyable life can be and Sundays feel like a lot of other days now as opposed to waking up and immediately having that kind of anxiety as to “Well I better get prepared for the week.” Now it’s “How can I enjoy Sunday? How can I enjoy the day? What can I do that’s going to bring me happiness?” as opposed to “What can I do to get ready for the next day?” And by realizing that each day is that ability to be grateful and realize that there is a purpose for me, I think, is what changed.

One should always ask themselves what is the legacy that we’re going to leave, each of us, and think we have an opportunity to think about that every day and I would just encourage people to really think about what it is that they feel when it’s all, you know, said and done that they did that mattered. I would just say that you only have one life and use your passion for whatever it is and create your own purpose in life. But think of when you’re on your deathbed or when people are thinking about you at the end of your life, what is it that they think about? And my guess is, at least for me, it wasn’t “I should have spent one more day in the office” or “I should have bought one more thing to put on my car.” And so, I would encourage people to think about that.

And if you say you can’t do it, that may be totally fair but, you know, ask why and really think about if those are legitimate reasons why you can’t do something and then challenge those assumptions to see if there might be an opportunity to change things.

You know, we all make money and we all look at sort of projected earnings, and we have to decide is there a point where our projected earnings are truly less and the opportunity cost, that cost of missing out on what could be with one’s life. And for me, I got to that point and I think as other people get to that point, there should always be an opportunity to at least ask yourself like “Okay, what would happen if I walked out today? I know the income I’d lose but what do I gain?” And I think that that’s just the point that people myself really found that was the critical sort of juncture where I decided that it’s time for me to do something else.

And so I knew that if I worked with you and we were able to sort of get to that core and for me to be true to my core, it was time for me to do something else. So it was really how does one pivot in life but maintain their core attributes, you know, as they say in Hamlet, “To thine own self be true.” And that to me is sort of what I carry with me and that was what freed me to be able to make the decisions that I made.

Richard Janes Commentary: When you go through a fundamental shift and what was once your own reality for a large part of your life, it often opens up the opportunity to look at other areas. Seeing places to double down on or places that simply need to be cut out, it’s the challenge that comes with change and in Ian’s case, as he lent more interconnection, he realized that the pact he had made with Wall Street wasn’t worth the price. And at 3:15 in the morning as he sat in his downtown Los Angeles office, he took a deep breath and pushed that ‘send’ button on an email that had gone through many, many drafts.

Ian Winer: My number one fear before I left was financial. And now that I’m out without an income, I can honestly say it’s probably the least of my concerns. I kind of have the mentality of, you know, “I’ll figure it out” when we get back from our volunteer work. The importance of carrying the message and as far as income, I realized that, you know, I feel like I have enough talent and enough experience and enough good will with people and friends and relationships that whatever it is that I wind up doing to help with income will be fine and it will all work out. And I think it’s a huge leap of faith but I do believe that the income just feels like you get wrapped into that and it becomes never enough and now that I’m not making any money, I’m starting to realize like “Okay, the world is still spinning” and life’s still going along and it’s all okay. You know, it’s just not necessary for me to sit there and beat myself up about the fact that I could be making a few more dollars today and I’m not because at the end of life, I don’t think it really matters how much money I’ve made or how much money I’ve spent.

Richard Janes Commentary: That junction where you decide it’s time for you to do something else. Most of us have had a thought like this at some point in our lives, that “what if”, that “if only” moment. But we chalk it up to fanciful thinking because life doesn’t work like that.

But what if those dreams you have could really become a reality? Now the truth is, the only person who is able to wave that magic wand, is you. Nobody is going to do it for you. And there are plenty of people out there living the dream so there’s no reason it can’t be you. The biggest thing that holds people back is themselves, and the key to getting out of your own way lies with listening to your heart.

When a baby is conceived, the first main organ to develop is the heart, followed by the brain. It’s heart before head. But in today’s society we put so much emphasis on the brain that we often relegate the heart energy until we can no longer hear its guiding song.

When we are solely in our head, we are dead. We second guess, we convince ourselves to keep the status quo. But we don’t have to. And as we think about the possibilities that tomorrow could hold for us, one of the biggest exercises is, as Ian found out for himself, is defining your own unique definition of success, what it means to you. Tap into your heart and start thinking about what success really means.

What does a successful life look like? What does a successful life feel like? Who do you have around you? What are you doing? How are you serving your community? Most of us have never taken the time to simply sit down and write what success looks like for ourselves. So we strop driving towards someone else’s mission, someone else’s vision of success where we are just the pawn ready to be played for the good of the overall game.

Ian Winer: To me, what matters is, the legacy and the willingness to try to make the world a little bit better. So for me, it’s how do I love people more? How am I a better husband? How am I a better person? What can I do that ever so slightly on the margin is going to make a positive difference for people? It’s not easy. I mean, it’s not like it’s just, “Well, forget it. I’m going to get rid of all of my stuff and none of it matters and, you know, I’m just going to focus on doing charity work the rest of my life.” It’s more that I’m realizing that doesn’t have to be how I define myself.

And that’s part of the adventure is, okay, so, when I go into Bali or I go to Sumatra, they’re not going to care that I ever drove a BMW that was murdered out. They’re going to care about “What am I doing?” I think to make things a little bit better. And so, that’s the real challenge. I can’t hide behind some of the stuff that I hid behind as sort of insulating from the outside world a bit.

Richard Janes Commentary: So I leave you today with these three questions: Do you have a purpose on this planet? Are you in touch with what you are passionate about? And when you’re on your deathbed, will you be able to say “I lived a life of passion and purpose”?

If you have trouble answering these, then I ask you, what’s stopping you from making the changes needed to lean into the very best version of yourself—a version of yourself full of passion and purpose. Just as Ian has done, are you willing to get out of your own way, embrace the fear of change and go on that adventure of discovery?

Richard Janes: Ian, thank you so much for joining us on the Passion & Purpose Podcast. We look forward to following you on social media as you gallivant around the world with your lovely wife Kelly. I look forward to having you back in a year’s time when the book is ready to be published.

Ian Winer: Can’t wait. And yes, thank you for all your help and thanks for the opportunity to chat tonight.

Richard Janes Author Portrait

podcast host: Richard Janes

Richard Janes is an Emmy winning personal brand expert with a passion for storytelling. His unique approach to personal branding has launched, revived, and catapulted the careers of many actors, athletes, musicians, television hosts, executives, and entrepreneurs.



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