Getting Real with Elliot Kallen — Prosperity Financial Group
28 Jan 2026 · 33 min
Podcast episode 'Getting Real with Elliot Cowen' (host Bill Gallagher) features a conversation with financial advisor Elliot Cowen about his career, leadership and scaling a financial services firm (Prosperity Financial Group), time management as a CEO, team structure, and a personal story: the 2015 suicide of his son Jake which led to founding the charity A Brighter Day to support teens with depression. Episode includes sponsor reads (Docsatalent, EO) and calls-to-action with links (abriterday.info, prosperity financial group).
Chapters
Are you thinking about how to grow your business with near and offshore staffing, but you're also wanting to make sure that it's reliable, cost effective, and really well done. I think docsa Talent is the way to go. Here's why. They don't just fill your jobs. They bring integrity, top talent, and a people first approach that's hard to find. I've known the people at Doxa talent for over 20 years now and I say that you can count on them. I have. Talk to Docs of Talent and you won't be disappointed. Go to docsatant.com Bill G Again, that's doxatant.com Bill G One more time. Doxatalent.com Bill G Check it out today.
Welcome again to the Scaling of Business podcast. This is a Getting Real episode. Today is really about, you know, the wisdom that comes from looking back and thinking about both where we're going and where we wanted to go and where we ended up. And talking with a great entrepreneur today about his reflections on all that's happened over his career and where things are going, integrating all aspects of life and that kind of thing. Hey hey everyone. I'm Bill Gallagher, Scaling Coach, host of the show. You can find hundreds of other episodes like this one on leadership and scaling up@scalingcoach.com we've got downloads of all the tools that we talk about in our show notes and we'll even send you a free copy of the bestselling book Scaling up right there@scalingcoach.com these getting real episodes on our podcast and livestream explore how our leadership has been shaped over time and by the growth of our businesses. What lucky breaks have we had? Have we navigated the breakdowns and surprises along the way? What has frightened us or embarrassed us as we've gone through growing our business? What are the things that we deeply regret? And where are we growing and developing today as leaders? This episode is sponsored by the Bay Area Entrepreneurs Organization Chapters, commonly known as eo. Our member led organization is the best place for entrepreneurs to find peers to connect with, to learn and grow with. And I'm proud to have been a member of this organization for the last 20 years as both a leader and a member across several different companies. EO members in the Bay Area are now supported and connected to over 14,000 members around the world, giving them an access to a whole world of entrepreneurship. If you'd like to apply for membership or get more information on EO, just visit eonetwork.org all right, listen in now as we talk with Elliot Cowen about his experience in growing his company and navigating that as an entrepreneur. Elliot, welcome to the show.
Great to be here, Bill, thank you.
Thanks for coming on. Elliot and I have become friends through the EO organization. So Elliot, you guys should know is in the financial services sector, investments and financial planning. He brings decades of experience in this and has built a couple of organizations before this. There's all kinds of technical things. I'll let him tell you a little bit about that. But I think you'll hear not only some of the business acumen but also his personal passions as we get into the conversation. So I'm glad Elliot is in East Bay. Elliot, where's your office?
San Ramon, California.
In San Ramon in the East Bay. East of San Francisco. So welcome to, we have listeners all over the world. Welcome to show Elliot. Talk a little bit about your getting started, the beginning of your career and give us a little background on, you know, childhood years.
I, I'm, I feel like I've had a very blessed life. I, I am the son of an Auschwitz survivor, concentration camp survivor and a great depression survivor made there and what they did is they taught the value of hard work and ethics and honesty and integrity. And for 20 years I had done that or so upon graduating from college as an accountant and then eventually as an owning an environmental cleanup business in 1993 I saw the end of that environmental cleanup industry happening as all the Superfund money disappeared. I had an accounting background and I made a decision that I was going back into the financial world, particularly financial services and or investment banking. And I was living in New Jersey at the time. My wife was pregnant with our twins and I and she's from California and she said I think it's time to move to California and raise our twins here, which is where I live now. So for the Most part in 1993 we wagon trailed out here, so to speak, cross country first through Michigan, then out here and then back and forth to pick up a car or two and hooked up with Lincoln Financial here in San Ramon. Oh yeah, started to build a career and again that was almost 28 years ago now. And sure enough 28 years later and breaking off and being our own registered investment advisory firm and having hundreds of clients. We're now a 300 plus million dollar organization in assets based in San Ramon just in the state of California and about the same amount outside the state in California where I'm a partner in and we're growing and now we also have a charity that we work with full time. So I'm CEO of three major organizations at this point.
And how many kids?
I have twins that are 27. And I had a 19 year old son who's no longer with us.
Yeah, we'll get into that story and in a few minutes. You know. So my grandfather actually. Well, both my grandfathers lived through the Depression. One of them was a banker and. And I think more affected by the other one by it than the other grandfather. One grandfather grew up on a farm and I don't remember hearing the Depression as formative as for the other like in terms of the stories. But, but my grandfather from LA who lived in a tent in the backyard. Right. Because extended family was occupying the rest of the house. He's the one who was more marked by the Depression and he was determined to die a millionaire even though he wasn't an entrepreneur and didn't have a particularly high paying career. He was a bank manager. Bank executive in a day when that wasn't as lucrative as it maybe is for some. But he was passionate about spending and being careful about saving and using credit really carefully. And it was so burned into him. And I just remember hearing about it at a young age. I'm curious, what are the lessons of both. What do you remember? How did, how do they transfer a thing, the lessons of the Depression and surviving something as horrifying as Auschwitz to you?
Well, if I go to my dad who was a Depression, you were a baby. They are a young man because he was born in 1915. So he was in his teenage years and was a small business entrepreneur. Never got past eighth grade. But he was determined to make good. And for him, what he taught us was, was the value of family. Everything about him was family comes first. Everything about him. So even our charity was going to help out other family members in their small businesses. And we had one, a close cousin of ours who owned a bicycle store. And on weekends my dad would loan us out to build his bicycles for him so he wouldn't have to pay for help. And that was good. And so it was a value of working. And from the time I was a little kid I wore a bow tie and I was his national sales manager and he bring me around all over from Boston to Philadelphia. And I'd have to tell the story about the human body and how the human heart worked because he was sure I was going to be the next doctor in the world. And it turned out that I really followed his footsteps as a businessman. But it was great, it was a great Learning experience about always be selling and then have the integrity and the honesty to sell something you believe in. So I think, I think that's a great lesson for mom. It's a totally different lesson for mom who was from Vienna and caught up in Theresienstadt and Auschwitz. It's about the value of ethics and thinking and hard work and using some type of forecasting in your brain to build something for your family. So again, family was central for her as well. But where are you going, what are you doing and how are you? Thinking was important for her. And very interesting, Bill, that for her English was her third language. It was German, French and then English. And she learned English from, for the most part, listening to the early days of talk radio, very early days of NBC and ABC and CBS on radio. And when she didn't know the word, she had her dictionary, Webster's dictionary, hardcover dictionary, next door, bed. And all night long she would look up words. And when she passed away, we buried her with her dictionary.
That's a bit of color. I used to keep a dictionary with me all the time and I use it. I probably have it somewhere here. But of course today we have the online dictionary so we can just quickly type in something. But I'll often find myself dealing with something at a surface level and I'll be like, yeah, but what does that really mean? And what else is implied by that word? Are there other uses of it? I find sometimes a single word can be pivotal in some idea that we're grappling with as a team.
I agree. For me, my thesaurus is my friend.
Finding another way to say something.
Yep.
Oh, interesting. So you're checking along and you get into this business. What is the, I don't know. What, what would you say is a lucky break that you've had?
I think the luckiest break I got while I was doing this was hooking up with some very good people that did some great training for me and kept me focused that. Between 8 and 5, you're doing business. You're not doing, you know, researching, you're not listening to cnbc, you're not reading the journal during business hours. That's what you do after hours. But during the day you're talking to prospects, you're talking to clients, you're sharing your story, and so you're putting in hard work. I've never known what a 40 hour work week is anyway, but I do research and I love what I do. So I start my day at five in the morning and I finished roughly it's six at night. It's a big day.
That's a big day.
Yeah.
So you get up at 5 or you get up earlier than 5?
I get up about 4:45.
Yeah. Interesting. Yeah. If I get up at 4:45, I'm like, my day's screwed up. I really need more sleep, Bill.
I don't drink caffeine, so it's even worse. I don't walk in to have a cup of coffee. I drink decaf because my staff gets afraid when I start drinking caffeine.
So you moderate even that and you work till six and then it's family time. Right.
I go home and I take over in the kitchen. My wife, who's terrific to me, I'm on my second marriage, Tammy's terrific. She gives me the kitchen and I take it over and I try to be an amateur gourmet chef. That's my separation of day and night.
So let's talk about the unlucky things or the challenges that you've had, some pretty substantial ones. Let's talk about the things that have really tested and developed you and how you've dealt with them. What would you like to share?
I could share the story of my son. That's probably most impactful, negative story for you, I'm sure. I mean, coming in during a recession 93 and dealing with the, the tech bot tech bubble in 2000. These will teach you how to keep clients and they'll teach you when you lose clients because they get upset about what happened today or what happened this week and you don't quite know what to do. But the real lessons are the life lessons. And, and that's. That taught me a lot. So in 2015, Bill, my sophomore son at the University of Montana, took his own life.
What was his name?
Jake. So we actually received from him Federal Express, a six page suicide note from him before we knew he was gone. And the first major paragraph said, mom and dad, I've been thinking about this for a long time. I never would have asked for your help. I never would have told you how I felt and I never would have taken your help. And while we flew up to Montana, Missoula to claim his body and bring it back to Lafayette for burial, I must have read that paragraph a hundred times. I realized as a parent and the last one to know what was really going on, my question to myself was, I wonder how many other parents are feeling this way. I wonder how many teens are feeling this way, not sharing this with their parents. And that's when we made A major decision to start a charity. So we began five years ago, a brighter day. And today, a brighter day.info has morphed into a charity that has helped thousands of teens with stress and depression, Giving out information and resources, touch their lives and have them get not so depressed that they're going to commit suicide and maybe talk to their parents or maybe seek out some help that can change their lives.
One of my other friends in the coaching world lost a son a couple of years ago, and it definitely has completely altered his life and his purpose in life. And I've shared in the past that I lost my father to suicide back in 2008. I think these things, they so, like, got us. There's nothing that prepares you for them. And even if you had, like my dad, I had some warning. There was a decline, and I was expecting it. But with a child, like, there's nothing.
No, we didn't know that. The only thing we knew was when he came home for the Christmas holiday break, he wasn't sleeping right. And then when he left to go back to school, he couldn't look me in the eyes. So I got very upset right away. I talked to his mother, and I said, I think I'm going up to Missoula. Something's striking me wrong. This doesn't feel right. And unfortunately, she kind of talked me out of it, Feeling that I was putting too much pressure on him to get good grades and. And that just let him be and he'll get through this. But he was a time bomb, and we didn't know it until it was too late.
You said his name, and I. His name's Jake. And my son's name is Jack, right?
Yeah, Jack, Jake. It's.
And every time a kid goes through something, you're like, what? What do I need? What can I do for them? And yet they have to find their own way.
You know, we had. We had suicide last week or two weeks ago in the Alkalonis high school district here, which is also where my son went. And the parents, again, were the last ones to know what was going on. No drugs, no alcohol. Just depression.
Yeah, depression. Right.
Alone.
Talk to us about the charity. What does the charity do? How do people get information on the charity like that?
Great. Thank you, Bill, for that opportunity. So the best place to get all that information is from the website. It's abriterday.info and all types of things are on there. But what we do for teens is we run teen talent showcases. So, you know, America's Got talent. Well, we took that concept, brought it to the team level. Well, we've done them live for a few years now, but now with COVID we turned that into teens that can submit literally any act. Juggling, skateboarding bands, piano playing, whatever that is. And at the end of it, we judge these monthly and the winners will go to a special final and then the top three finalists get college scholarships. So the last year we gave out eight college scholarships and our, our goal is to pay for books for four years of college.
Oh, that's really cool though. For viewers, for listeners, the link will be in the show notes and for viewers, it's on the screen right now. A brighter day.info right there. If you want to see more about the program and what they do and, and how they're helping kids and families deal with depression and try to reduce some of the things that happen. How has that changed the way you interact with your team, your clients, that kind of thing, that life experience? Aside from actually creating the charity, what do you notice in your day to day kinds of things, your human interactions?
Bill I'm touched by the amount of people who have a story to share about their, their brother, their sister, like you, their cousin, their child. They're all bad stories, by the way. There's, it's not like there's a good story unless somebody's gotten some help. There's no good story to suicide. There's no mind son did, did a worse job than your son or there's just no upside there. And so what it's done is I share this story and I've woven it through. What we do is it's create a level of integrity that people know that there's somebody that cares, there's a team that cares about you. And that was true before, but now we have a story to tell about this. And so when I talk to people, it is amazing how many people I meet with that have a tear in their eye because they have a similar story or a story about depression or a story about cutting or, or story about bullying. And those are all things that we have resources for, but they're all stories that need help. Teens are going through the toughest time ever right now and we can't cure that. Teens sitting in San Ramon. But we can give out some resources that maybe the teen and the parent can get some help. And with our clients, they know we're out there to help them.
I think it's really great because lots of times teens aren't willing to or any age Young adult, young person are unwilling to be helped by the parents. They want to figure something out, they don't want to talk about it, but someone else they might be open to. The friends aren't always that helpful or productive. Sometimes they're downright dangerous. Right. In the remedies that they suggest, behaviors and drugs and things like that, they sometimes don't. But having some other resource, some other outlet that, that cares beyond the parent who they may not be willing to open up to. As, as you got in your, in your letter, right?
Absolutely. You know, teens naturally are self absorbed. So it's really hard for a teenager to think about your life because they're too busy thinking about their own. So we do have tools for teens to help their friends if they recognize it. But even when it's really interesting when, when the one year anniversary, almost the one year anniversary came around and we did an unveiling for my son's plaque at Oakmont Cemetery, a number of his fellow students and friends came from Montana for it and they asked if they could interview me for college credit. And we went to Noah's Bagels and we did an interview. And it wasn't an interview at all. It was an apology from them for not noticing, for not realizing what was going on, for being so wrapped up in their studies, in their world that they couldn't see that Jake was tired when they were awake and awake when they were tired, they couldn't see it. And his hockey coach and he played hockey, Montana set all types of records. His hockey coach told me that he scored. He passed away on a early, early Friday morning at about 1:45 in the morning. Earlier that week on a Tuesday, he scored seven goals in one game. But that wasn't enough. You know, that was great at the moment, but that was short lived or lived. And so his hockey coach didn't see it either.
Well, so I hear more connection, more empathy and your develop capacity to be vulnerable and to go into areas that we don't often talk about. We often avoid things that are uncomfortable and distressing like, like depression and suicide.
Absolutely.
People and, and yet it reinforces what matters in, in the business. What. So looking back on this and in the other parts of your life, what do you notice that you're grateful for now as you've growing your business over time?
Well, I'm going to start again with family. You know, I've had the fortunate life of having three children. I have a now with a second marriage which is terrific. I have a stepson that I'm Close with, he's married. So I have a daughter in law. They have. She's pregnant, eight months pregnant. So that's wonderful. I've got a stepdaughter with an 8 year old grandson that lives with us. Got a fabulous relationship with him and I'm the main man in his life which is great. So that right off the bat that's what I'm most grateful for. And in business I've had the fortunate experience of creating teams. So I have a whole team here that works just in my California market to support our business. I have a team dedicated to outside the state of California to support our business. And we now have a senior executive director and executive director for a charity that can do the day to day in charity work that needs to be done. So thankfully again I'm supported by very talented people who care as much as I care.
I get that. Is there something that you could share that most people don't know about you?
Other than I'm scared to death of snakes. So it's actually a funny story for another day but I've had three run ins with poisonous snakes in my life and you know, it's, it's left me.
Have you ever been?
No, but I've been within inches of being bitten. If a poisonous steak was on the ground, I'd be dancing on my desk because I'd be as far away as I could be right now. But no, I think the lessons here and what are and the downside is, you know, when you're an entrepreneur and I know I'm talking to many entrepreneurs, it's very rarely a straight line in life. How business goes and how life goes. I always thought in my life I'd have a fairly straight lineup. I'd get married, I'd have children, I'd buy a house, I'd build a business up, maybe I'd sell them by another business or I just would grow and grow and grow and you know, and in 50 years I'd be retired, you know, get my Rolex watch and be playing golf and you know, my life has been anything but a straight line. It's has been business challenges in there, it's been selling businesses, it's been keeping liabilities, it's been paying off banks, it's been growing and it's been an adversity many, many times as it's been as I just explained some of them. So my lesson really is you're going to get kicked down, you're going to get knocked down. It's kind of out of The Rocky movies. It's not how many times you get knocked down, it's how many times you get back up and keep fighting. I did steal that from Rocky. So it's. I, I think the lessons here is when life is not a straight line, keep fighting, keep swinging the bat. You might hit singles and doubles. You also might hit some home runs. And that's my life lesson is don't stop swinging the bat. Don't. Whatever your sports metaphor is, whether it's boxing or baseball or football, keep playing.
It's funny how often we use sports metaphors, not big sports fans. So if you were to look back at your younger self, is there something that you would do differently or advice that you would have for your own younger self in about your career?
Yeah, I think, you know, when I was in college, Bill and I, and that's the lesson, I parted with my, my children. I said I had a dual major at Rutgers. I was both an economics major and an accounting major. And I liked economics more. And I. But to be an economist, you have to get a master's degree. And in those days, you got a master's degree right out of college. Today, it's a little bit different. But accounting represented immediate income, a job right out of college in a world of money. And so my father sat down with me and he said, whatever you do, do not be an accountant. It's not your personality. You're not sitting at a desk. You're not adding up and tabulating all day. And I had my internship at college where I literally got graded for tabulate. My, how fast my fingers work on a calculator. They actually graded you, but that did represent money. So instead of going for another 18 months.
Did you suck at the calculator?
I have lightning fingers. I was 40 words a minute in, in college, in high school, already on my fingers. Okay. But I liked economics more, but I turned it down because I wanted the immediate money. So I got a job in accounting. And that was a mistake because I didn't stay there all that long. It wasn't for me. I should have done economics. So I, I overruled my common sense and my father's advice for immediate income. And to this day, I wish I didn't.
So listen to dad.
That's the lesson. Yeah. My best friend who graduated as an accountant, went by, graduated as economist, went back and got an MBA in finance. And today he's worth hundreds of millions of dollars.
So I, I hear one. Listen to Dad. I also hear, don't go for the quick Money. Pursue what you really care about. Right. The bigger, longer term thing.
Yeah. And if I had the right vision, which I didn't at 21 and 23, I would have done it differently.
Yeah. Now what are you working on now? What's your big goal now?
So we are 300 million in California. I've got a five year plan to get that to $1 billion in assets under management. So we're scaling up, Bill, as to use your phrase, to grow the company. And at that point we can do almost anything we want with a company. A billion dollar company can be sold, can be merged, can be anything can be done with it. And that's the long term goal, is to put this company at some point in play by either buying other people out or merging into a multibillion dollar entity. But that's a good five to ten year plan.
Now it'll take some time. And what do you think is your challenge or gap? Like what are you struggling with as you pursue the billion assets? What do you not know how to do yet to get there?
So a CEO. The greatest challenge I think we have as CEOs is time management.
Yeah.
As I'm running three organizations every day, one takes 80% most of the day, which is the good side, Prosperity Financial Group. The other two a little less. But on days that they need help, they could take an entire day or two. And now I'm ignoring my core business. So it is just balancing. Sometimes I feel like I'm in the old Ed Sullivan show as the man spinning the pie plates on top of the sticks. So it's just having enough time and people around me to do the right job.
So when and have you ever looked at are you doing the most valuable right things versus just being busy or working on time wasting things?
I look at that and I don't always like what I see.
Good, good answer. How many people on your team now with the main business?
Well, I've got five independent advisors and I've got a staff of three. And then I've got a marketing department now with three, so six there that's just California. Outside of California we've got 40 individual advisors or so and two people working in that business outside of California.
And is that split that way for regulatory reasons?
It's. We just run it as two separate entities.
So learning how to use your time more effective. And who are you? Who do you look up to? Where are you going to develop yourself in this capacity? How are you working on getting better at time management?
So it's not that I'm bad at time management is that I've. Like entrepreneurs, sometimes you're just so busy putting out fires, you're not working on what you need to do. Yeah. And so I, I do, I have hired consultants in the past that hold people's feet, including my own, to the fire. That helps something you do as well as your business. How to scale up and prioritize. I, I think the issue that we all have as business owners is what's important and what's right now. And they're not necessarily the same thing. So I have my staff meeting almost every day in the morning at 8 in the morning, and we talk about priorities today just to try to keep us all on track. Because it's not just me, it's everybody. We got to stay on track.
The daily huddle is so transformative. I want to. Before we move on, I want to remind our listeners and viewers that this episode is sponsored by the Bay Area Entrepreneurs Organization, commonly known as eo. This member led organization is the best place for entrepreneurs to find peers to connect, to learn, to grow with, to hear stories about how they're doing with it. Both either to validate what you're going through and how you're approaching it, or to come up with some new approaches. Right. I'm proud to have been a member of this organization for over 20 years now and through several different companies. The EO members of the Bay Area are supported and connected now with over 14,000 around the world. That gives them a whole access to a world of entrepreneurship that is just so unique and so unusual. I know like very well, have good friends with entrepreneurs in every continent and in dozens and dozens of cities today because of that lifetime of membership in the EO organization. If you'd like to apply for membership or if you'd like to get more information on EO, just visit eonetwork.org.
What.
Are some final thoughts or things that we should be talking about that we haven't talked about? Elliot?
I think, Bill, I think in our business, and I try to tell everybody that people ask me, they said, what attracts you? What attracts clients to you? And why do they stay with you? And so, you know, you think that at the core we're trying to be good money managers, good stewards of people's finances. But that's not why people stay with us. They really stay with us because they have trust. And I think for any business owner, no matter what business you're in, I would say integrity and honesty are important. But trust is why you keep your clients, do they trust you that you trust your team? Because when trust goes away, it doesn't matter if I earned them X percent over whatever the stock market was. It's gone, it's over. You can't get it back.
So that's actually a great topic. And we have another show on that. I'm just looking to see when that is. It's in two weeks. We've got a show about trust with David Horsager and it's just a great, great conversation, great show. So I highly recommend folks check that show out in a couple weeks. Coming up, I also want to remind folks where to get in touch with you. So if you want to hear see more about Elliot's business and the charity. So it's a brighterday.info and Prosperity Financial Group, we'll put in the crawl right there on the video and we'll put it in the show notes down below so we've got a link. Go right to it. So Prosperity Financial Group, you want to find out about Elliot's business and what they do and so on. And, and then also the charity organization a brighter day.info both right there. Elliot, thank you so much for coming on and talking with us today about, about your life, your business and sharing vulnerably about some of the things that you've had to deal with. I really, really appreciate it. I want to remind our listeners and viewers that if our show helped you in some way, please turn it on to somebody else. Pass the love, pass the value around. Of course it helps us if you, if you give us a review and, and say something nice wherever you get it. But if you are a subscriber to the show, you send us an email to influence info@scalingcoach.com and show us that you subscribe. Take a screenshot of YouTube or iTunes or go to scalingcoach.com wherever you do that, we'll send you a special set of unreleased tools and worksheets that are useful for helping your company grow and scale. I want to give special thanks to Vern Harnish, author and creator of the Scaling Up Framework and the original Rockefeller Habits. Our show is produced by Lucas Lucy Summers, working in the background here, throwing up things on the screen and getting our guests prepped and our show scheduled and that kind of thing. The show's audio is edited by Albert Burge at Podfly Productions and our show notes are written up by Ein Kodina and proofread by Tim McGowan. Thanks again for listening and watching everyone we'll talk to you next time.
Keep scaling up thank you Bill. Foreign.
Are you ready to turn your goals into daily wins? You should check out our Scoreboard software powered by Align. It's the official software for scaling up. With Scoreboard you'll get an AI driven coach for priorities and KPIs and it'll help keep your team focused on what matters most. With Align you can track your goals in real time and you'll even see results on the go with their mobile app. You can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software, it's what I actually use to manage growth in our scaling up client teams. Unlock clarity and results with Scoreboard by Aligned. To try it now go to aligntoday.com Bill G One more time aligntoday.com Bill G that's aligntoday.com Bill G Check it out and try it now.




