November 23, 2025 • 13 mins
We spoke with Founder and CEO of Brave Enough to Fail, about how the organization prepares tomorrow's leaders and gives students the confidence and actionable steps to achieve their biggest dreams.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Good morning. My name is Alison Demurz. My guest today
is Wayne Winsley. He is CEO and founder of Brave
Enough to Fail. Good morning Olson.
Speaker 2 (00:10):
Thank you so very much for having me on today.
Speaker 1 (00:12):
Oh it's my pleasure for those who don't know about
Brave Enough to Fail. How did it come about?
Speaker 2 (00:18):
Well, to put it in context, IM gonna tell you
just a quick bit about myself. I'm originally from Cleveland, Ohio,
and I was raised by a single parent, my great grandma,
And when she got too old to take care of me,
I ended up in the welfare system. I was an
orphanage for a while and boys down for a while,
and along the way I failed eighth grade the first
(00:39):
time and second time around. I'm walking around, skipping school,
shoplifting out of stores to get food and stuff like that.
And the thing that changed the trajecting of my life
was over her conversation. Her friend of mine's dad was
talking to him, and what he said was, I don't
care what you do, but be at excellent at something
(01:01):
will overcome poverty, prejudice, and adversity every time. Descrive for excellence.
And for whatever reason, that message stuck in my head
and Based on that conversation, I chose to go back
to school and actually work at it. Didn't become an
instant straight a student because I'd been disengaged for like
two years, but I got to amazing bes and some
(01:23):
things see student in math. But I celebrated seventy life.
It was one hundred from long story short, I graduated
from high school, didn't end up in prison at a cemetery,
yet served my country honorably in two tours in the
US Navy, and went on to enjoy a twenty year
career in broadcasting here in Connecticut. So I'm living proof
(01:45):
that a message can change the trajectory of a child's life.
And my goal with Brave Enough to Fail is bringing
that message of hope to as many young people as
possible and giving them the courage to go after their dreams.
And brave enough to Fail simply means being brave enough
to risk failure is a non negotiable requirement for success
(02:08):
in any venture. Our goal is to give students the
courage to take their shot of their dreams, give them
some educational tools to help them do it, and some
scholarship money to get him started.
Speaker 1 (02:19):
Well, God bless you, and God bless your grandma absolutely
and your mess became a message.
Speaker 2 (02:27):
It did, and in that story, that foundation of my life,
that's my why, that is why we do what we do.
Speaker 1 (02:36):
So that led you to start brave enough to fail,
and you have what's called the Boss Academy. What is that?
Speaker 2 (02:43):
Boss Academy is a twelve session course that drills down
and gives students the tools to actually go after their dreams.
Boss is built on four pillars that sell the word Boss.
The B is for big dreams in life. Your results
are never going to rise above your expectations, So you
(03:04):
got a dream big. The oh it's for getting out
of your comfort zone. You want to get results you
never gotten. You got to do things you never done.
The first S is for strategy, a plan to get
where you want to go. A dream without a strategy
is just a fantasy. And the second ASS is for
stick to itiveness, the perseverance to keep going and not
quick when it gets hard, because it's going to. When
(03:26):
we tell our students that second S is so important
that without it, the first three letters won't work. You
can have a big dream, get out of your comfort zone,
have a strategy, but once you give up and throw
in the towel. It's done. So our course teaches things
like goal setting, strength analysis, effective communication, time management, mental toughness,
(03:51):
self motivation, all those success skills that are so necessary
no matter what field or endeavor you're going into.
Speaker 1 (03:59):
So how can RUS receive this or become involved?
Speaker 2 (04:02):
The great part of it is our programs are at
no cost to schools or students. For a school to
get BOSS Academy, they have to request it, submit a
written request on their letterhead, and with that we take
that to our funders and the great people that support us,
and that allows us to get the funds to provide
(04:25):
the programs to the schools and students. And so far,
since twenty fifteen, we've reached just over forty thousand students
and we've awarded just over one hundred and twenty five
thousand dollars in scholarships.
Speaker 1 (04:39):
Wow, that's amazing. What kind of scholarships are available?
Speaker 2 (04:43):
The scholarships are good towards tuition at any accredited college
or trade school, because not everyone needs to go to college.
Speaker 1 (04:50):
And I love that you say that not everybody needs
to go to college? Is not for everyone?
Speaker 2 (04:55):
No, it is not.
Speaker 1 (04:56):
So you also have a presentation that you bring to schools.
Claw well, be the Boss of your Dream. What does
that entail?
Speaker 2 (05:03):
Yes, be the Boss of your Dream is an assembly
style motivational presentation that gets students fired up and encouraged
about whatever dream is in their hearts. It is a
great lead in we find two providing the Boss Academy
program the schools because it lets students know what it
is and it makes them excited to take part in
(05:26):
it when they realize, oh, wait a minute, this isn't
just like more of work, because who wants more work?
But this is something that is cool and for me
to get what I want? And that is the goal
of the be the Boss of your Dream presentation. The
idea is, Alison, I cannot achieve your dream for you
(05:49):
or reach your destiny for you. You have to do it yourself.
Speaker 1 (05:52):
Tell me what kind of impact has it had on
the students or the families who have benefited from all
of these programs.
Speaker 2 (05:59):
Well, we have. We have gotten some tremendous, tremendous response
from students. We have Boss Academy scholars that are off
the college. Now we have we've been doing this long enough. Now,
we've been doing for ten years, we have Boss Academy scholars.
(06:20):
One of them is an investment banker at Barkley Bank.
One of our scholars is a software developer for Amazon,
and one of the associate producers of Late Night with
Seth Myers is a Boss Academy scholar, and in fact,
one of our scholars serves on our board of directors now.
And we have been running our Boss Academy now for
(06:43):
the past five years. At our longest running which is
at Faith Preparatory School in New Milford p Tech Norwalk
High School. Are in their third year and the feedback
from the administrators there is that it has become a
part of the culture of a Walk High School and
Boss Academy is referred to as the coolest club at
(07:05):
the school.
Speaker 1 (07:05):
That must make you feel so good.
Speaker 2 (07:08):
It is just the wonderful, the most wonderful feeling I
have to share with you. The first time I did
a site visit after we started our program at Norwalk
High School and the principal and when the counselors took
me around and to see our program being taught by
student leaders in classroom after classroom because they use it
(07:29):
as their advisory period. Alison, I almost cried.
Speaker 1 (07:33):
Did you ever think all these years later that everything
you went through would be used for good?
Speaker 2 (07:40):
I have no idea, and you know, as as a
man of faith, I have to say, you can't see
God's plan, but you can look back and see the
evidence of it. And everything that happened to me made
me the person that I am, and one of the
greatest things I can say. I look back and I say,
you know what I was this kid. I used to
(08:02):
walk past the campus of Cleveland Community College in downtown
Cleveland and think that college was for people not like me,
people who were luckier than me, whiter than me, whatever,
just not me. And now I'm a Aimizian where I
actually am helping other kids go to college.
Speaker 1 (08:25):
That's wonderful, It's really really beautiful. You say that motivation,
not just money, decides student success. What do you mean
by that?
Speaker 2 (08:34):
Because Allison, do you do you have children?
Speaker 1 (08:37):
I have children and a grandson. I'm a nana.
Speaker 2 (08:41):
Wow also young. Oh well, well, so, so here's here's
the thing. There is not a program in the world
that will make your child or your grandchild do their
homework if they flat out don't want to. Nothing, But
even a fail does is. It gives students a reason
(09:05):
to want to because it's based on what they want.
We start by telling students that that dream, that faintness
in your heart, it is important. It matters. You are
unique and priceless with a destiny that only you can fulfill.
And we just merely suggest that you can use your
education as a tool to get that thing that you want,
(09:28):
and we will show you how to leverage it.
Speaker 1 (09:31):
And that's why confidence is so important. Self esteem.
Speaker 2 (09:35):
Absolutely, you have to believe that you have because you
believe what you tell yourself about yourself more than you
believe anything than anybody else says about you.
Speaker 1 (09:48):
That's right. How can people donate or support you?
Speaker 2 (09:51):
You can certainly go to our website and we thank
you so much because again we're only able to provide
our service at no cost to school in students because
of the generosity of those that support us. Our website
is brave enough to fail dot org. Also, we are
a part of the PayPal Giving Fund, so if you
(10:12):
go to our website and give through PayPal, there's no fees.
One percent of your donation goes directly to our programs.
Speaker 1 (10:20):
And what are the ages of the children to the
students that you serve.
Speaker 2 (10:24):
We serve middle school and high school. We are grades
seven through twelve. Uh. And the interesting that you say
that because at Faith PEP Faith Preparatory in New Milford
and at Scatacoke Middle School in New Milford, it's used
as an in school elective and it is for the
(10:47):
middle school for said grades seven and eight. You know,
our goal now is to expand our program and reach
as many students as we can. Uh. We just launched
a new state of the art a website that allows
us to provide our programming to schools throughout Connecticut.
Speaker 1 (11:07):
Wonderful. How can people donate or support?
Speaker 2 (11:11):
Our website is brave enough to fail dot org and
you can certainly go there and make a donation. And
we are part of the PayPal giving fund, so if
you donate through PayPal on our website, there's no fees.
One hundred percent of your support goes directly to programming.
Speaker 1 (11:30):
Do you ever need volunteers, Yes, we do.
Speaker 2 (11:33):
We always have room for volunteers. One of the other
really cool things that we do, and this is where
volunteers can be really key. At Boss Academy, students can
get real world experiential knowledge and wisdom from people who
are actually successful in careers that they're interested in. What
(11:54):
that means is. For instance, Alison, you are a broadcaster.
In a fifteen minute zoom interview, you could share with students, Matt,
this is what I do. This is how I got
to do this thing. These are a couple of things
I had overcome in my life and here's how you
could do it too, if this is of interest to you.
And we have people from professional athletes to entrepreneurs, doctors, lawyers,
(12:20):
investment bankers, all giving the wisdom of their experience through
our video mentors, which is part of our curriculum. That's
one of the things that sets us apart.
Speaker 1 (12:32):
I love that I hear it all the time every
time I do an interview, people who say to somebody else,
I've been where you are. I got through it. You
can get through it too, and this is how I
did it.
Speaker 2 (12:41):
Absolutely. You know. I tell people, I said, you know,
if you could get twelve millionaires in a room to
tell you how they became successful, how expensive would that
consultancy be thousands of dollars? Well, Boss Academy, our students
get that kind of knowledge for free because of the
(13:04):
generosity of the people that provide the time to do it.
For instance, for one of our students in Bridgeport, Okay,
at Harding High School, where is a Harding High School student?
Typically when would they have an opportunity to sit down
and hear from the CEO of an investment house in
Manhattan and would it that's not their circle. You don't
(13:24):
have access to people like that, But at Boss Academy
you can, and that is how we level the playing
field of access with Boss Academy.
Speaker 1 (13:33):
I'm speaking with CEO and founder Wayne Winsley of Brave
Enough to Fail. All of these programs and services you
can find at their website brave Enough to Fail dot org.
You can volunteer, you can donate. Thank you so much
for being here today and for serving our children.
Speaker 2 (13:50):
Alison, thank you so very much for helping us get
the word out. Thank you so very very much.
Good morning. My name is Alison Demurz. My guest today
is Wayne Winsley. He is CEO and founder of Brave
Enough to Fail. Good morning Olson.
Speaker 2 (00:10):
Thank you so very much for having me on today.
Speaker 1 (00:12):
Oh it's my pleasure for those who don't know about
Brave Enough to Fail. How did it come about?
Speaker 2 (00:18):
Well, to put it in context, IM gonna tell you
just a quick bit about myself. I'm originally from Cleveland, Ohio,
and I was raised by a single parent, my great grandma,
And when she got too old to take care of me,
I ended up in the welfare system. I was an
orphanage for a while and boys down for a while,
and along the way I failed eighth grade the first
(00:39):
time and second time around. I'm walking around, skipping school,
shoplifting out of stores to get food and stuff like that.
And the thing that changed the trajecting of my life
was over her conversation. Her friend of mine's dad was
talking to him, and what he said was, I don't
care what you do, but be at excellent at something
(01:01):
will overcome poverty, prejudice, and adversity every time. Descrive for excellence.
And for whatever reason, that message stuck in my head
and Based on that conversation, I chose to go back
to school and actually work at it. Didn't become an
instant straight a student because I'd been disengaged for like
two years, but I got to amazing bes and some
(01:23):
things see student in math. But I celebrated seventy life.
It was one hundred from long story short, I graduated
from high school, didn't end up in prison at a cemetery,
yet served my country honorably in two tours in the
US Navy, and went on to enjoy a twenty year
career in broadcasting here in Connecticut. So I'm living proof
(01:45):
that a message can change the trajectory of a child's life.
And my goal with Brave Enough to Fail is bringing
that message of hope to as many young people as
possible and giving them the courage to go after their dreams.
And brave enough to Fail simply means being brave enough
to risk failure is a non negotiable requirement for success
(02:08):
in any venture. Our goal is to give students the
courage to take their shot of their dreams, give them
some educational tools to help them do it, and some
scholarship money to get him started.
Speaker 1 (02:19):
Well, God bless you, and God bless your grandma absolutely
and your mess became a message.
Speaker 2 (02:27):
It did, and in that story, that foundation of my life,
that's my why, that is why we do what we do.
Speaker 1 (02:36):
So that led you to start brave enough to fail,
and you have what's called the Boss Academy. What is that?
Speaker 2 (02:43):
Boss Academy is a twelve session course that drills down
and gives students the tools to actually go after their dreams.
Boss is built on four pillars that sell the word Boss.
The B is for big dreams in life. Your results
are never going to rise above your expectations, So you
(03:04):
got a dream big. The oh it's for getting out
of your comfort zone. You want to get results you
never gotten. You got to do things you never done.
The first S is for strategy, a plan to get
where you want to go. A dream without a strategy
is just a fantasy. And the second ASS is for
stick to itiveness, the perseverance to keep going and not
quick when it gets hard, because it's going to. When
(03:26):
we tell our students that second S is so important
that without it, the first three letters won't work. You
can have a big dream, get out of your comfort zone,
have a strategy, but once you give up and throw
in the towel. It's done. So our course teaches things
like goal setting, strength analysis, effective communication, time management, mental toughness,
(03:51):
self motivation, all those success skills that are so necessary
no matter what field or endeavor you're going into.
Speaker 1 (03:59):
So how can RUS receive this or become involved?
Speaker 2 (04:02):
The great part of it is our programs are at
no cost to schools or students. For a school to
get BOSS Academy, they have to request it, submit a
written request on their letterhead, and with that we take
that to our funders and the great people that support us,
and that allows us to get the funds to provide
(04:25):
the programs to the schools and students. And so far,
since twenty fifteen, we've reached just over forty thousand students
and we've awarded just over one hundred and twenty five
thousand dollars in scholarships.
Speaker 1 (04:39):
Wow, that's amazing. What kind of scholarships are available?
Speaker 2 (04:43):
The scholarships are good towards tuition at any accredited college
or trade school, because not everyone needs to go to college.
Speaker 1 (04:50):
And I love that you say that not everybody needs
to go to college? Is not for everyone?
Speaker 2 (04:55):
No, it is not.
Speaker 1 (04:56):
So you also have a presentation that you bring to schools.
Claw well, be the Boss of your Dream. What does
that entail?
Speaker 2 (05:03):
Yes, be the Boss of your Dream is an assembly
style motivational presentation that gets students fired up and encouraged
about whatever dream is in their hearts. It is a
great lead in we find two providing the Boss Academy
program the schools because it lets students know what it
is and it makes them excited to take part in
(05:26):
it when they realize, oh, wait a minute, this isn't
just like more of work, because who wants more work?
But this is something that is cool and for me
to get what I want? And that is the goal
of the be the Boss of your Dream presentation. The
idea is, Alison, I cannot achieve your dream for you
(05:49):
or reach your destiny for you. You have to do it yourself.
Speaker 1 (05:52):
Tell me what kind of impact has it had on
the students or the families who have benefited from all
of these programs.
Speaker 2 (05:59):
Well, we have. We have gotten some tremendous, tremendous response
from students. We have Boss Academy scholars that are off
the college. Now we have we've been doing this long enough. Now,
we've been doing for ten years, we have Boss Academy scholars.
(06:20):
One of them is an investment banker at Barkley Bank.
One of our scholars is a software developer for Amazon,
and one of the associate producers of Late Night with
Seth Myers is a Boss Academy scholar, and in fact,
one of our scholars serves on our board of directors now.
And we have been running our Boss Academy now for
(06:43):
the past five years. At our longest running which is
at Faith Preparatory School in New Milford p Tech Norwalk
High School. Are in their third year and the feedback
from the administrators there is that it has become a
part of the culture of a Walk High School and
Boss Academy is referred to as the coolest club at
(07:05):
the school.
Speaker 1 (07:05):
That must make you feel so good.
Speaker 2 (07:08):
It is just the wonderful, the most wonderful feeling I
have to share with you. The first time I did
a site visit after we started our program at Norwalk
High School and the principal and when the counselors took
me around and to see our program being taught by
student leaders in classroom after classroom because they use it
(07:29):
as their advisory period. Alison, I almost cried.
Speaker 1 (07:33):
Did you ever think all these years later that everything
you went through would be used for good?
Speaker 2 (07:40):
I have no idea, and you know, as as a
man of faith, I have to say, you can't see
God's plan, but you can look back and see the
evidence of it. And everything that happened to me made
me the person that I am, and one of the
greatest things I can say. I look back and I say,
you know what I was this kid. I used to
(08:02):
walk past the campus of Cleveland Community College in downtown
Cleveland and think that college was for people not like me,
people who were luckier than me, whiter than me, whatever,
just not me. And now I'm a Aimizian where I
actually am helping other kids go to college.
Speaker 1 (08:25):
That's wonderful, It's really really beautiful. You say that motivation,
not just money, decides student success. What do you mean
by that?
Speaker 2 (08:34):
Because Allison, do you do you have children?
Speaker 1 (08:37):
I have children and a grandson. I'm a nana.
Speaker 2 (08:41):
Wow also young. Oh well, well, so, so here's here's
the thing. There is not a program in the world
that will make your child or your grandchild do their
homework if they flat out don't want to. Nothing, But
even a fail does is. It gives students a reason
(09:05):
to want to because it's based on what they want.
We start by telling students that that dream, that faintness
in your heart, it is important. It matters. You are
unique and priceless with a destiny that only you can fulfill.
And we just merely suggest that you can use your
education as a tool to get that thing that you want,
(09:28):
and we will show you how to leverage it.
Speaker 1 (09:31):
And that's why confidence is so important. Self esteem.
Speaker 2 (09:35):
Absolutely, you have to believe that you have because you
believe what you tell yourself about yourself more than you
believe anything than anybody else says about you.
Speaker 1 (09:48):
That's right. How can people donate or support you?
Speaker 2 (09:51):
You can certainly go to our website and we thank
you so much because again we're only able to provide
our service at no cost to school in students because
of the generosity of those that support us. Our website
is brave enough to fail dot org. Also, we are
a part of the PayPal Giving Fund, so if you
(10:12):
go to our website and give through PayPal, there's no fees.
One percent of your donation goes directly to our programs.
Speaker 1 (10:20):
And what are the ages of the children to the
students that you serve.
Speaker 2 (10:24):
We serve middle school and high school. We are grades
seven through twelve. Uh. And the interesting that you say
that because at Faith PEP Faith Preparatory in New Milford
and at Scatacoke Middle School in New Milford, it's used
as an in school elective and it is for the
(10:47):
middle school for said grades seven and eight. You know,
our goal now is to expand our program and reach
as many students as we can. Uh. We just launched
a new state of the art a website that allows
us to provide our programming to schools throughout Connecticut.
Speaker 1 (11:07):
Wonderful. How can people donate or support?
Speaker 2 (11:11):
Our website is brave enough to fail dot org and
you can certainly go there and make a donation. And
we are part of the PayPal giving fund, so if
you donate through PayPal on our website, there's no fees.
One hundred percent of your support goes directly to programming.
Speaker 1 (11:30):
Do you ever need volunteers, Yes, we do.
Speaker 2 (11:33):
We always have room for volunteers. One of the other
really cool things that we do, and this is where
volunteers can be really key. At Boss Academy, students can
get real world experiential knowledge and wisdom from people who
are actually successful in careers that they're interested in. What
(11:54):
that means is. For instance, Alison, you are a broadcaster.
In a fifteen minute zoom interview, you could share with students, Matt,
this is what I do. This is how I got
to do this thing. These are a couple of things
I had overcome in my life and here's how you
could do it too, if this is of interest to you.
And we have people from professional athletes to entrepreneurs, doctors, lawyers,
(12:20):
investment bankers, all giving the wisdom of their experience through
our video mentors, which is part of our curriculum. That's
one of the things that sets us apart.
Speaker 1 (12:32):
I love that I hear it all the time every
time I do an interview, people who say to somebody else,
I've been where you are. I got through it. You
can get through it too, and this is how I
did it.
Speaker 2 (12:41):
Absolutely. You know. I tell people, I said, you know,
if you could get twelve millionaires in a room to
tell you how they became successful, how expensive would that
consultancy be thousands of dollars? Well, Boss Academy, our students
get that kind of knowledge for free because of the
(13:04):
generosity of the people that provide the time to do it.
For instance, for one of our students in Bridgeport, Okay,
at Harding High School, where is a Harding High School student?
Typically when would they have an opportunity to sit down
and hear from the CEO of an investment house in
Manhattan and would it that's not their circle. You don't
(13:24):
have access to people like that, But at Boss Academy
you can, and that is how we level the playing
field of access with Boss Academy.
Speaker 1 (13:33):
I'm speaking with CEO and founder Wayne Winsley of Brave
Enough to Fail. All of these programs and services you
can find at their website brave Enough to Fail dot org.
You can volunteer, you can donate. Thank you so much
for being here today and for serving our children.
Speaker 2 (13:50):
Alison, thank you so very much for helping us get
the word out. Thank you so very very much.
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