Trading Secrets - 76: Kelley Flanagan: From an attorney to influencing, Bachelor fan favorite reveals the power in connections, the impact of family dynamics, and the unknowns of life with Lyme disease
Episode Date: October 31, 2022This week, Jason is joined by one of Bachelor Nation’s favorite personalities, Kelley Flanagan! Kelley gained recognition after being on Peter Weber’s season of The Bachelor and although sh...e did not win Peter’s heart on the show, the two of them have reconciled after the show and have become one of Bachelor Nation’s favorite couples. Outside of her time on the show, Kelley has developed a very distinguished career as an attorney as well as establishing a social media following of over 1 million followers between Instagram and TikTok. Kelley gives insights to her time at boarding school Culver Academies with a vast variety of important people and how it shaped her, how maintaining relationships is key, why she is investing her money from influencing instead of spending, and what life looks like with Lyme disease. Kelley also reveals her parents upbringing and how her dad instilled the importance of education and knowledge, the highs and lows of working with family, her love of travel, sticking with careers you enjoy, and if she sees herself becoming a CEO or owning an entire business. Does she consider herself to be more of an introvert or extrovert? What kind of law does Kelley’s family practice? What does she want out of her professional life? Who got sued from Peter’s season regarding a giveaway? Kelley reveals all that and so much more in another episode you can’t afford to miss! Be sure to follow the Trading Secrets Podcast on Instagram & join the Facebook group. Host: Jason Tartick Voice of Viewer: David Arduin Executive Producer: Evan Sahr Produced by Dear Media. Please note that this episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products or services referred to in this episode.
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The following podcast is a Dear Media production.
Welcome back to another episode of Trading Secrets.
Today I am joined by one of Bachelor Nation's favorite personalities and one of my great personal friends, Kelly Flanagan.
Kelly gained recognition after being on Peter Weber's season of The Bachelor back in 2019,
2020.
And although Kelly did not win Peter's heart on the show, the two of them have reconciled
after the show and become one of Bachelor Nation's favorite couples.
Outside of her time on the show, Kelly has developed a very distinguished career as an attorney
and has also established a social media following of over one million followers between
Instagram and TikTok.
Today, we're going to discuss her experiences on The Bachelor, what her career is an attorney looks like, life is an influencer, in all the ways that she has been able to capitalize financially on her huge platform.
Kelly Flanagan, thank you so much for being here.
We are excited to have you on showing secrets.
Thank you.
I appreciate you guys having me.
I'm not going to lie.
I am exhausted, so I might be a little bit boring, but I'm going to do my best.
And why are you shot?
What's going on?
I mean, last night, we all had dinner.
And it was great.
You, Evan, Peter.
Yeah.
We stayed out late.
Did you stay?
Did you guys go continue your ass?
No.
No, we literally went home.
You know, I wasn't, I didn't drink all day yesterday.
It's not even about that.
Did you not drink at all?
No.
Not even at dinner.
I barely do.
I barely ever drink.
It's just like not my thing.
But I don't know.
Lately I've been exhausted and shot and I don't know if it's my Lyme disease.
And I'm sure we'll get more into that.
But it just hits me out of the blue.
And it's like I almost can't function because I get so tired.
like no for no reason see i like when that and i feel that especially because this is like a
you know more of a business type podcast yeah i want to like tap into that because it impacts
everything yeah it impacts how you are professionally it impacts your work for sure it impacts yourself
with a partner like the worst thing i want is to be around people that i'm not like a hundred
percent comfortable with yeah when i'm in these moods because i get like i get moody sure i get like
short and then people are always like oh my god like why is she being that way and i was like you
guys just have no idea how I feel. So like when I'm out with my friends and they bring like a
newcomer in, I'm like, this is the last thing I want. And it's not necessarily, it's just too much
because I can't like to put on that facade and like act great. It takes a lot of energy when you're
in this mood. So yeah, I could be a loner at times. Do you think that that is like a, I think
that's a thing within this world like the reality television thing creates. I think it creates
this thing where you have this extreme paranoia like you're always just worried about making
impression because you just never know I don't know where it's going to go if someone says
anything yeah and then you feel like you always have to be on but being on just drains your
batteries like have you felt any of that since you left the show yeah of course and and that
comes from the show but this is even like more I would say exclusive than that like even if
I'm with my friends and they bring like a new friend around you know what I mean like
having to sit there and have a conversation with them and me being like super
super, super exhaust to the point where I could probably fall asleep right there.
It's like, I don't want this newcomer to come around and be like, oh, this is my friend Kelly.
You know, I've spoken so highly about her and I'm just a dud.
Yeah, yeah, yeah, totally, totally.
You know, so it's just hard.
When it comes to, like, meeting people or fans, like, on the street, it's very easy to put on for two seconds.
Hey, how are you?
Good.
Okay, like, yeah, let's get a picture.
But when it's actually, like, I have to drag along a conversation and talk to them and not feeling well, that's when that's when.
That's a lot.
I'm just curious.
Now my curiosity is driving me.
Would you consider yourself an introvert or an extrovert?
It's funny because it just depends on the way I feel like I could be.
I'm sorry, that's my phone.
We got anyone good over there?
No.
I mean, the reason I say anyone good because Kelly's contact list is outrageous, we will talk about networking next.
It's insanity.
Before we get into that, are you an introverted or extroverted?
I would say I'm more introverted than extroverted.
I definitely like to have fun and socializing.
and stuff like that, but definitely more introverted.
Interesting.
Yeah, because a lot of people wouldn't guess that.
Because when I am out and I do have energy, I would say, like, I can't have, like, high
energy.
Like, hey, how are you?
What's going on?
But then, yeah, no, it's more introverted.
And, like, we'll get, we're going to get into your work stuff.
But even on the show, I think, in an Instagram stuff, you come off as extroverted.
Yeah.
You come off as like, I'm going to say how it is.
I'm fearful of nothing.
This is who I am.
Like, I'm Kelly the attorney.
Watch out bitches.
And you would say that you don't think that that that that's what it is.
No, I'm not.
That's not Kelly Flanning.
No.
Okay.
I'm sure at dinner with all of us last night, you were probably like, God, this girl speaks her mind so much.
No, I loved.
I mean, that's actually, you know, I don't want to get too much into that world, but it is part of your world.
Just being with like you and Peter and Evan and stuff.
I just loved how open discussion was.
Oh, yeah.
And I think if you can have an open discussion like that, it also creates so much.
ease in a relationship because you know where you're staying.
Yeah.
Right?
No, for sure.
I'm very blunt.
I love it.
She's blunt.
All right, let's get into you always being on because there's a great story, a great story
from yesterday.
Okay, so I finished my podcast and I finish at 530 and I'm with my producer Evan.
And Evan says, I'm going to the Yankees game.
And I say, Evan, you're out of your mind.
You're going to arrive there at 630.
You're going to catch two innings and you have to go 45 minutes there, 45 minutes back.
I'm not going.
He goes, that's fine.
I'm going.
So he goes, he does his thing, and I knew he was in good hands.
That's why I left him because I knew he was going to be with you and Peter, and he loves you guys.
So I wasn't like leaving him hanging.
So he gets there, and then he shows me your seats.
Seats like, they were okay.
They were average, you know, not the best seats in the world, not the worst seats in the world, but you're at the Yankees' playoff game.
And I said, you know what?
He's going to catch three innings.
I made the right choice.
All of a sudden, I get a text of a video of the biggest suite I've ever seen in a text from Evan Tsar saying,
we are in the Steinbrenner suite at the Yankees game.
I started motherfucking era.
What the fuck?
How did I fuck this up?
And then they were explaining that you actually went to boarding school with the Steinbrenner's daughter.
Yeah.
And it's just your network is next level.
I mean, tell everybody just a little bit about like what is Kelly like as a networker.
Is it intentional?
Is it because you went to school?
Do you have a certain thing that you apply to it?
How do you fucking know everybody?
I would say, I would say,
definitely both. One, I was fortunate enough growing up that I was just placed in crazy,
crazy places where, you know, a lot of really successful people have been. Between my boarding
school, it was really cool. There would be people all over the world. You know, I was dating a guy
out in the Middle East. Like, when are you ever going to meet someone in the Middle East? And,
you know, I had a lot of friends from Mexico. I had a lot of friends from Asia. But a lot of people
send their kids to this, like, prestigious boarding school.
is this morning school? It's called Culver Academies. It's in Indiana. It's actually military for the
guys. Oh, so you weren't in Chicago. No, it was in Indiana in the middle of a cornfield. So what's
cool about it is a lot of like really important people will come there, but they can't necessarily
have that ego behind them because everyone is in a uniform. You can't like put on, you know,
you can't use your money to your benefit. Like a lot of people in New York, oh, I got a table here,
be my friend, all that stuff. When you're in the middle of a cornfield with people who do come from a lot
of stuff or don't come from a lot of stuff. Like you, you can't really tell because no one was able
to flaunt their money or use it to their benefit. Like, we're in a cornfield. Like, you want to go play
volleyball. Like, you want to go play baseball. Like, you didn't really have too many options. But
what's really cool about that boarding school is since you don't have many things to do, you get
to know everyone on such a personal level that, like, it doesn't matter if you don't see them for
10 years. Like, you're, you still know, like, their heart, you know who they are. You know
them at their core. Because you're essentially living with them, you know. So what's the deal?
Just help me out here. I feel like the voice of your, David, you're going to love that.
The Curious Canadian. I know you met David. He's a beauty. What is the difference of a prep school
and a boarding school? Is there a difference? Don't quote me on this, but from what I think the
difference is, is a boarding school, there's like more boarding students. So like the students are
actually living on campus. Got it. So like, again, we had people all over, you know, I think it was 95
percent of the people were actually living on that campus versus like day students were like going
back home to their parents' house and stuff like that. Like I was living in a dorm with three other
girls as, you know, the majority of the campus was doing as well. So you, okay, you're living there
full time. Why in your head, like when you graduate middle school, at any capacity were you thinking like,
I'll go to a private school in Chicago or I'll go to the public school? Was it always set that
you were going to the board school? I think I knew from third grade, you know, there was definitely more
pressure when I have five older siblings and all of them go through there. So they all went to
they all went there. So when I was I think in third grade, I was like, I'm going here. And again,
my parents never put pressure on us in the sense that they would be like you're forced to go here.
But yeah, it was just more of like I felt the pressure because I had to essentially like do what all of
them did. Like it would be weird for me to be the only one to not choose that. And I saw how like much
it benefited you. Like it made you grow up fast. So it was military for the boy.
boys, but also the girls had to follow some of like the military rules.
So like every morning we would get our uniforms checked, like someone would come in,
make sure it was like appropriate.
We would have to like make our bed, clean our room.
Every morning you would get checked.
So we had to follow like some of the military guidelines all throughout high school.
And yeah, it was just a crazy experience.
I remember I saluted.
So a lot of these teachers that are there, a lot of them were like, you know,
used to be in the military for 25 years or something.
crazy like that. And I was just being like a stupid high school student. I think I saluted one of like the lieutenants or, you know, one of the teachers and I saluted him the wrong way. And I almost got detention for that one because he took so much offense. And like, I didn't really know what I was doing. I was just being an idiot. But like again, that's something not to necessarily joke about. But, you know, I wasn't thinking in the moment. So when I did that, he was just like, how dare you? And he like ripped me over and I heard. I heard. You got a mouthful. Yeah. What is what is what do you? I mean, you. I mean, you. It's, it's, what do you. I mean, it's. It's.
I mean, the Steinbrenner's went to your school and a lot of big names have gone to your school.
What does it cost?
I think when I was going there, it was maybe like 35, $35,000.
Again, I feel, again, very fortunate, but feel bad for my dad having to put six kids through that and then college and then law school.
Imagine that.
He did boarding school for us and then he did college for all of us and then he did five law school.
Because all you guys are attorneys, all five years.
yeah so we dad's a hero and a legend we ripped him trying to talk to about this because most people
like myself hear that and we're like I don't understand I'm still trying to grasp the concept of
boarding school yeah so when when people are paying you the Steinbrenners all these people
they want their kids to go to boarding school what is what's kind of the thought why is the boarding
school the play like what's the return what's the end oh I god I can go on for hours on this one
And I'm going to be honest with you
When I first went there
Again, I'm the youngest of six
I was kind of a little bit more
Like I would get away with murder at home
Because my parents are older
They started super late to have kids
My dad like kind of already made his success at that point
But when he was grinding
Like he wasn't married, he didn't have kids
So he was able to just like focus mainly on that
But I like there were so many times
Where I'd be like screaming every dorm has like a counselor
So like the counselor if you get in trouble
You gotta go to them
And there would be times I would be, like, running down and being like, I hate this place because it was so strict.
And I was used to like, I don't know.
Freedom.
You know what I mean?
Like going on AIM and messaging my friends.
You know, here, internet shuts out at, or you have, you have, God, what is it called, CQ, which is study hours.
I think that was from 730 to 930.
We had no cell phones.
Your phone, like your dorm phone would have to be out in the hallway.
So you're studying nonstop.
And then after 930, you get 15 minutes.
Like if you had a boyfriend or a friend or had to run out of your dorm, you had 15 minutes until 9.45, you got to come back in.
The door is locked. If you're late, you get detention. Lights out at 10.30. So people walk by, make sure your lights are out, make sure you're sleeping. So it was like a huge adjustment for me. You know what I mean? Like internet shuts out. Internet shuts out. I think it was at 10.30. And it would just be like, oh, my God. Okay. Like, I wasn't used to that. How strict it was. You know, your room had to be clean every single morning. Like, you would get inspected. Like, think about that. It's a lot of pressure for a 14-year-old child.
doing like your laundry you had to learn how to do that like you know a lot of a lot of these
people that came from maybe wealthier backgrounds or didn't have the best upbringing in terms of
like their parents being there for them like sure it creates structure in you and not only that
like culver was very big on making sure that like all of their teachers were just like the best
of the best so they again they're living on campus if you weren't doing well in a class like
you couldn't get away from your teachers you see them at lunch you see them at lunch you see
him at dinner. You see him around campus. Where are you going to go? So, like, they would invite you to
their house and being like, if you're struggling, you're going to come in and I'm going to like
teach us to you. So it was just so strict. And then we had like a leadership program within the
school. So like you had a dorm, you had like a dorm chair. So like the girl in the dorm would be
ahead of or she would be in charge of her dorm. You would have like a bunch of different positions.
And so you had to take like leadership and learn how to essentially like lead other people.
And you had like people below you.
So it was usually like the juniors and seniors, the freshmen and sophomores would be the people that you were leading.
So it was just like at the age of 14, you really knew how to just like live by yourself.
You know, mommy and daddy aren't doing anything for you.
So it was a super accelerated thing.
We're at 14.
Most Americans, I'm thinking, are probably experiencing this in like 18, 19 in college.
You guys are experiencing it at 14.
So it accelerates your path, I feel like.
And then I feel like the other thing, the biggest take.
way I'm thinking about is a lot of these individuals have parents that are working literally 24-7
and probably have a nanny their whole life growing up. So as a result of that, the idea of maybe
the discipline and the attention that's needed at that level is less than existent. And this
creates that. And not only that, I think the biggest thing that I took away from it is
maintaining relationships. You just learn, like if you are, you know, a lot of people can go to school,
they could be the shy kid, they come back to mommy and daddy and just their siblings and you're fine.
You got to go to the school. You now know no one. You might have some siblings there, but at the
same time, like, you have to learn how to make yourself happy in that situation. Like, you can't
rely on anyone else. Like, you have to learn how to make friends because you're going to be living
with them. You have to learn how to maintain them, respect them, because you could blow them real
fast. You know, like, if you screw someone over, you're going to see them the next day.
Yeah, totally. So it's like you learn loyalty, you learn friendships, you learn how to maintain
friendships you learn just essentially and they're so it's so diverse there in terms of just like
where everyone comes from you learn so much about their culture about what you like about what you
don't like and it just like makes you a little bit more open minded because I was just like oh my
God like you're from you know Asia tell me about this like how do you guys do this how do you do
that and it would be cool spring break you would go you would visit them and I just experienced so much
at such a young age, but was able to kind of learn how to make myself happy and also learn
like my likes and dislikes and just about other people culture, other people's cultures
and how people differ.
Interesting.
Okay.
So, I mean, to be in that type of school and obviously your dad put you guys through that,
let's just call space, spade.
There's a lot of wealth there to be able to do that.
Was that with your father, did he start the law firm or where did it all come from?
So I'll actually be honest. My dad had an extremely hard upbringing, and my mom did too. My mom, you know, came from the mountains of Greece, was playing with, like, Lambones as toys, like, had no hot water, no running water. And she was the manager at Jewel, like, working her ass off. She had two jobs to get her degree. Her parents, she would come home. She's Greek. Her parents would, like, beat the crap out of her because a woman wasn't supposed to get a degree. She was paying rent in her own house. And my dad had, you know, my dad didn't come from anything. And historically,
it was a little different. It was more of a trophy wife situation where like my grandma was this
like beautiful blonde bombshell from Finland. And my grandpa was like, I think she was like 23. And then
my grandpa was like six years old and, you know, a very Irish Chicago guy. So his mom kind of left him
really young because she wasn't ready to like raise kids. So she left and he was raised by his
grandma, his Finnish grandma. And then the dad was still kind of like going around Chicago doing his
thing. So he, like, loved my dad and his brother, but, like, wasn't necessarily there day to day.
Sure. So then my dad actually went to, he got sent off to a boarding school a little bit more just
because of, you know, people were busy and didn't necessarily, like, want to take care of him.
Yeah.
And he still kind of has, like, nightmares from it. Like, you know, trains go by. And it's, like, PTSD because he was so
upset when he would, like, go by these, that he was there, knowing that, like, that was the case.
But he went to a rival of Culver that actually shut down.
But, you know, he, when he became successful in his own right, you know, he worked his ass off to start a law firm.
He was an assistant state's attorney in Chicago.
Wow.
And was working with, like, Mayor Daly, like, you know, the mayor of Chicago back then.
And he just made himself super, super well connected.
And he just kind of got thrown this opportunity to be like, why am I not in this space of law?
So he started it. He had no family. You know, he didn't have a wife. He didn't have kids. So all he had was time on his hands to entertain clients to start his law firm. And he killed it. And he's doing really well. But that was all on his own?
That's amazing. And so was it instilled in you guys, like your family, you guys are all going to go be attorneys? Like you're going to go to law school?
No. No. Because all you guys did. And I've seen clips of you. I've never met your siblings, but super sharp dudes.
Like everyone is like, you know, sharp as a deck.
That wasn't instilled.
That wasn't like you're going to law school.
No, I think my, again, my dad's like the nicest guy you'll ever meet.
Like, he's just so kind.
My mom's more of like the little go-getter who's a little feisty.
But no, my dad would always, you know, say education's the most important thing.
Like if you have some kind of just like knowledge behind you, you could do anything.
You know what I mean?
Like he was so big on education.
So he would always push us.
And there was times, I think one of my brothers almost failed fifth grade.
because he had 32 missing assignments.
So, like, we were not great children, you know?
Like, we were messing up a lot.
But my dad would always kind of just push, like, you know, make sure you have some kind
of background, make sure that you're always, like, educating yourself in some degree.
And then, yeah, he just, he would definitely say the pros of it and, like, sell us on them.
And being like, listen, it just makes you think different the way, like, it is just so beneficial
to have that knowledge behind you.
So, you know, my first brother decided my second brother didn't.
So my second brother is not an attorney.
And then all of the rest of us followed track.
But it was, it was, I would say I didn't know what I was doing.
Okay.
I wasn't, you know, one of my brothers, he knew since he was like four years old.
He's like, I'll give it a show.
Everyone's, that's the direction I've seen of success.
I'm going to go.
Yeah.
All your other family members that have done it other than your one brother, are they all working for your dad?
Yes.
Okay. And your other brother who didn't do it, what does he do?
He is a farmer.
And does he? Really? Wow.
Yeah. He's like obsessive with plants.
Interesting. Yeah.
Okay. And so that's a wild. That's why I'm taken back by that. Okay.
But you also be taken back because you would think like, okay, all of them are attorneys. No, my brothers are big.
Like, we have farm out in Illinois and they go and they love hunting, but like they're like creating their own ecosystem out there and they're buying pheasants.
They're buying bats, like the bats to eat.
I think like the ticks or something.
Yeah, like a whole entire sense of stuff.
They're literally trying to start their own ecosystem out there.
Like they grow farm.
They grow like, so it's, my family is very different from what you would think like a typical attorney is.
Like they're goons, they're idiots.
But, you know.
I love it.
It's very well balanced.
So then you go to, by the way, I love that you went to the University of Alabama.
Something we never learned on the show or after.
So you go to University of Alabama, you get your degree.
do you consider going to other law firms to work or do you immediately say I'm definitely going to
your family's office?
When I got to my family law firm, I really, I'm huge in traveling.
I love traveling and I kind of wanted to go to London.
So I was trying to figure out if I could go use my law degree over there.
And then I was like, you know what, let's give this a shot.
So I started working for my family to see if I liked it.
It started taking more courses because what they essentially do isn't totally law
related, there's other things involved with it. So I started taking more courses to like learn the
ropes. No, I would have been happy there. I definitely would have been happy staying there. But
yeah, I think I was just in a period of, you know, what am I doing? And then I decided to go on the show.
And so your family, though, they're in tax a lot, right? Yeah. Tax a lot. Okay.
They do property tax appeals for commercial real estate. So essentially like a lot of people don't
understand that, but like say you have a really big building, some kind of skyscraper building. They
essentially go and they do the taxes on those buildings because every year those buildings have
millions of dollars of taxes to pay. Of course. And like the government essentially comes and says
something along lines of like, hey, this is what your taxes are going to be. And what my family
does is they essentially help these companies get it down to some kind of like mediation price or
negotiation price that like actually is fair. Because they just put a big stamp on you and say,
hey, this is what you owe. So we appeal them and we say, no, actually we don't owe that much because
this, that and the other.
Based on X, Y, and Z law.
Yeah, and when you're dealing with millions of dollars, you know, it's a lot for these companies.
Huge impact.
Got it.
Okay.
So you go to work and then the question I got asked before the show, how the hell do you sit
there, I with your dad, who put you in boarding school at 35K a year, put you through
Alabama, put you through law school, and try and negotiate your salary?
Like, what the hell does that look like?
No, we, so we all knew that, like, again, with me, like, everything was already set in stone.
Like, you know, my dad was, he was, like, paying rent, and then he was paying my phone bills and then my health insurance and stuff like that.
And when you started there, did you ever actually think in 10, like we talk about career navigation and pay transparency on this podcast, did you actually think in 10 years from then you'd still be an working attorney?
That's a good question.
I've always kind of, like, never really knew, you know, where I'd be.
I don't think like that.
Like, I know other people, like, for example, Peter's like, I wanted to be a pilot since I was four.
And I was like, I've never worked like that.
I've never been like attached to something so much that like this is what I'm going to do for the rest of my life.
Like right now I'm doing influencing stuff.
Who knows what I'll be doing in six months?
Who knows what I'll be doing in a year?
I have no clue.
I just have never gotten attached.
So like what do you like dream six months from?
I can't even tell you.
You don't know.
I can't tell you.
I kind of love that.
Yeah.
I just like.
So how do you know that you're doing is right?
Because I enjoy it.
Okay.
If I don't enjoy it, then I don't enjoy it.
it's time to switch something up and I'll figure it out.
And do you enjoy, well, we're going to get into the show for a minute, just like about
the career changes, but do you thoroughly enjoy the work that you do now?
Yeah.
What do you enjoy most about it?
The freedom.
The freedom's incredible.
Yeah.
And not only that, but freedom, you have to understand that, like, again, I was working with
all my siblings, so they're sitting there and one of my brothers is the biggest asshole sometimes.
I'm not going to lie.
But, like, he would be like, go get my car wash.
wouldn't. He would be like, okay, like, we're going to take away this from you, take away that
from you. So they would kind of like, it was kind of like I was their little puppeteer that would
have to do everything they said or they would start limiting. You were like the intern because
you're the youngest one. Not even the intern. It would be like personal stuff. Like go clean this.
And again, I'm exaggerating. Yeah, of course. It would be things that were not law related to any
degree. And then like if I didn't listen, he would be like, okay, like, we're not going to give you
this or they would like just try to like you know what i mean like limit me in certain ways and i was
like oh god so it was like constantly in fear of kind of my own family to some degree because
my oldest brother could be such a bully like he really is but just now knowing that like i could
work when i want do what i want i'm making great money and i don't have someone essentially
i don't know telling me what to do in that sense yeah i think guys at home the one thing that's
really important. I grew up with a lot of families. I think the affluent families, at least in a small
town like Buffalo, they have made it because most of them, not everyone, but most of them have
family businesses there, and it's been a generational thing. And you would expect a lot of those
businesses to have like just sweet Jesus meals every day, living the life, things are good,
everything's bliss, rainbows and roses. And the stories I've heard internally from a lot of
of these family offices where you think everything's picture perfect are things that are a hundred
times worse than I ever heard in the corporate world. And so I do think that's good to like give
some visibility into that. Family businesses, while extremely can be lucrative and great and
everything else, like it could be really tough too. It could be really hard. You're balancing a lot.
Who gets what? Is there an ego issue with that? Who's taking over? I mean, there's a lot that goes
into that stuff. What I'm fortunate about is there are six of us. So we all, we all know each other's
flaw is pretty well but we're actually so close and yes we will go off on each other and we'll
tell each other like you suck all this stuff but we actually get along so well that like none of us
will leave any anyone out to dry which is such a cool feeling because you know for how much I
complain about my brothers like they help me so much I like I can't thank them enough and they're just
like it's so cool to have a soundboard to just go to and being like hey like I'm stuck with this
decision like what do I do and everything they they say like it I'm like you're you're smart
like things I need that like it makes sense like they're just smart individuals that you could trust
so so when you were offered the opportunity to go on the reality show the bachelor at this point
when they're carting you around saying go do this go do that to you is it a no brainer are you
thinking through it oh no I thought through it because they were on top of me they didn't want you to
go yeah some did some didn't it was like a 50-50 split who and your family wanted you to go who didn't
my dad had no idea what it meant what did mom think my my dad like oh my mom was excited
she was thrilled half was like like I remember one of them and he's probably like the most low
key was like go through the process like it'd be fun like but don't actually do it my other brother
who's sweet the farmer he was just like do whatever you want and then my two other brothers were
like absolutely not was there any risk in like again higher profile of the
family. You guys have a lot of big clients. You're getting fucking snuck into this
dime renter suite. That goes on. I mean, was there anybody in the family like you can ruin
our reputation? Oh, absolutely. Because not only that, with my family, like, again, people who own
commercial real estate, it's the 1%, you know? So not only that, like, our clientele is the 1%
because they're all owning, you know, we're dealing with commercial real estate. So my brothers are
extremely, extremely well connected because these are their clients. So like that's why I know
lot of these people, too.
Got it.
So I'm essentially hanging out with our clients.
And again, they have connections and stuff like that.
So that's why you're like, what is happening here?
But again, like, think about our clientele.
And my brothers have to constantly, like, be around those type of people.
I forgot where I was going with this.
We were talking about a little bit about the impact of you going on the show.
And just like, yeah.
So, yeah.
So they're dealing with like, they're dealing with really high profile people who are probably
pretty judgmental.
Yeah.
And there's probably concerned about that.
So, yeah, they were definitely concerned.
And then, you know, I just kind of decided I was like,
I've never, like, changed my opinion if I feel strongly about it to appease them.
I've never been that person.
You're just like, I'm going to write my own ticket.
All right.
Then I got to ask you this.
You go through the show, and you're, especially on Peter's season and Bachelor,
you were, I would say, if it's fair to say, extremely likable, but polarizing.
Like, when you thought something, you set it.
You're just like, this is who I am, deal with it, take it or leave it.
Were there any professional, that's all I want to know, professional repercussions or pushback
from your family, given the way the show appeared?
No, actually, they didn't care at all.
Like, I remember getting off the show, and I think they tried to, like, not give me the best
edit in some degree, but it actually was fine.
Like, I was okay with it.
You know, I could read through some of the stuff that, like, didn't necessarily go down
that way, but I was like, oh, whatever.
Definitely not your average reality star, that's for sure.
And believe me, the producers told me that right from the jump.
They're like, we love you.
But, man, you were not like a good contestant.
I was like, yeah, I understand.
Like, I get it.
Lose your shit.
Do what we tell you did.
Yeah.
And I was like, no.
So you finished the show.
And I was curious about the reputation risk if they had any problem.
You said that they didn't have any problem.
They didn't.
And I was actually surprised by that.
Sorry, that's where I was going.
I was actually surprised because a lot of like our clientele was actually like so happy.
So now, yeah.
They were like, let's go Cal.
Yeah.
Yeah.
which I was shocked about.
Wow. So it actually worked in your favorite. I mean, not really, but it like makes them, like, love that affiliation.
Did you find, again, trying to stick to the business side of this, did you find that having a family with a lot of success and, you know, you've learned to carry yourself a certain way?
Did that work against you at all with the house or the entire show just seeing like a confident, professionally successful person in a position where they're like, I don't need.
this, but I'm here if it works out.
I think everyone knew that was my mentality, but again, like, I'm going to watch
my words. I'm not going to, like, put that in people's face or, like, make them feel
that way. So, like, they would pick up on some things. Like, when I'd be like, my sister plays
polo and my brothers play a lot of golf. Like, people are going to read in that and be like,
who is this rich little brat? But I genuinely don't think I, like, carry myself when I'm
talking to people. I don't, like, sit there and, like, purposely bring it up to make you feel
lesser about yourself, like, or I'm not going to sit there and, like, act like, a brat.
Like, there's a lot of people that maybe haven't known my background and they're like, they've been shocked to hear like when they start like hearing through the great vine of things.
And they're like, what the heck?
Yeah, because I just don't carry myself that way.
Like if, yeah, I'm sure there's like bratty parts of me and, you know, but again, like I've always been called out.
Like, anytime I got a purse and a designer purse, I think I have like two.
And, you know, I could afford them now now that I'm doing my own thing.
But like, I just don't really care.
Sure.
Yeah.
But anytime I would have, like, anything designer, like, my mom would, like, just, like, beat the shit out of us.
She'd be like, what is wrong with you?
I haven't raised you this way.
If we were raised by my dad, we'd be spoiled brats.
Yeah, yeah, yeah.
But my mom definitely kept this in check.
Yeah.
Did you think about going back to law work after you finished The Bachelor?
Yeah, yeah, I was.
And did you?
I did for a little bit.
And then what was the breaking point that made you say, you know what?
I'm done with this.
I think when you see, like, the finances coming through.
The numbers.
When you see the numbers coming through from social media.
And I was like, man, like, I can get away from my brother's being mean to me and be successful in my own right.
This is great.
Since you left the law firm to go do social media work, have you had any regrets or do you have any desire to be an attorney again?
Yeah, I do.
And you know what?
There are times where I miss just like the stimulation, just like the mental stimulation that you get.
And, again, it's, like, painful going to law school.
And you're like, this sucks.
But when you're done with it, like, I was looking.
at some of my law stuff. And I was like, man, it's like kind of hard to read this stuff now.
You know what I mean? Like you, you kind of lose it if you're not using it. Totally. And I miss
that. I miss like, it's kind of just like this challenge in your head when you figure out how to
put like A, B, and C together type of thing. You're like, oh my God, like it's rewarding.
Right. So when you're not using your brain that much anymore, it made me miss it.
Got it. That makes it a lot. It's just the whole stimulation. It's a different world. It's a
creative angle. But it's not in the weeds.
And you're also not always dealing with the most stimulated people in this space.
Yeah, I just get ragged on all that.
But you were, I mean, yeah, yeah, you just got people chirping you every second about something.
My question to that is, what's your take on the future of it all?
Like, the money that's coming in now, do you ever get worried about, does this end?
Does this continue?
Yeah, for sure.
Will it last a year or two?
And then what is, do you think about what the professional plan would be then?
Like, how does Kelly interpret the navigation of this?
like wild wild west that i hear you and i definitely don't think it's going to be like it is now
and if that's the case like i'm not kidding jason every single penny that i have made i've invested
at it i invested every single penny that i have made like i'm not going and again like i'm i haven't
bought like a chanelle bag i don't even own a chanel bag can i go buy a five thousand dollar bag absolutely
but i would rather invest that than ever put it towards a bag like it just it like i don't know it just
would bother me to like waste money like that. And not only that, like in 2021, my parents were back
in Chicago. So I was just thinking like, okay, how to, you know, I'm making like really good
money for myself. I don't want to rely on my family in any degree. What do I do? I was living
out of my parents' house in Florida. And again, I know I'm fortunate enough to be able to do that.
Sure, sure. I know that's one of my something that many people don't have, but I was like,
you know what for that whole year when I am like making bank. Yeah. I'm not going to
pay rent. I'm going to go down there. And again, like, it was kind of lonely. I was essentially
living in, like, an old person's home for an entire year. But again, I travel so much, so it
didn't really matter. But I didn't pay rent for an entire year. So every penny I had coming
through, through social media, I took that money and I was just investing it. And again, like,
that's where my brother's coming to play is they're so smart when it comes to investing. So,
like, I might not necessarily know what to do, but they teach me. They tell me what to do. I
trust them. And yeah, so I've literally invested every penny for my future. So almost every
penny that's come from social media monetization has been invested.
Yeah.
It's unbelievable.
Yeah.
That's the Rob Grinkowski of the Bachelor of every dollar that's coming from his NFL contract
has gone into savings, which is amazing.
Ten years from now, professionally.
I know that's not your thing.
It's not your thing projecting.
But what does it look like?
Like the dream.
What is the dream to, 10 years from now to be a mother and just be with your?
That's an amazing thing.
But that's amazing.
No, it is amazing.
I don't work like that at all.
I can't peg you down.
I'm like moving left and right.
I'm like, what is it?
What is it she wants?
What do you want out of your professional life?
I genuinely like, we'll see.
And you know what?
Something like sparked me a little bit.
So one of the girls that was on my season,
I don't want to say her name because I just don't know if she wants to be named.
But she came to me.
And I think that I'm in a very special place that not many people understand.
Okay.
I have a law background.
and I also know social media like the back of my hand.
And I think there's a lot of rules and regulations coming into this field
that, you know, a 65-year-old guy who has no idea what Instagram is
is going to be dealing on these contracts, it's going to be, it's a different language.
Look what happened with Kim Kardashian.
Yeah.
SEC just came down on, for anyone that doesn't know, SEC just came down on Kim Kardashian,
and they came down on her because she was promoting a cryptocurrency,
and it wasn't done legally correctly.
Yeah.
Yeah, and she put hashtag ad on it and they still did it.
She did all the things she thought she did, which is all the things that we would have thought.
Oh, no, it was something along the lines if she didn't, she didn't put the money amount that she made from it.
Maybe she didn't put the money amount.
She didn't put how she was connected to it.
I think it was more of a go check out Ethereum and it was more of a blanket statement without any type of ad stuff.
So she settles with SVC for one point million something.
We'll hit that in the recap.
Stay tuned.
We'll talk all about that.
But from that, it has created this crazy ripple.
because now people are realizing this influencing thing is no fucking joke.
People are like blow it off, shake it off.
They're like, no, this is a massive, massive, huge multi-mult,
billion dollar business that is growing by the second.
And I think there's a lot of attorney work.
I'll tell you a quick story.
We do, obviously, we do a lot of financial banking, stuff like that.
After the Kim Kardashian thing, I'm not going to name the company, we had a banking company
reach out to us and say, hey, you did this.
for us in these dates and it was great and you complied with everything but where compliance is
today those are outdated you have to go remove them so this i'm talking like 2018 19 shit no way so yeah
heaven and i are sitting there like what the hell where it was we're digging through this and
we had to delete it all so to your point i'm sorry to interrupt no you're friend there is something
huge yeah with the legal world and social media oh yeah and i think it's i think it's going to take off
And again, the story I was telling one of the girls, it's the most ridiculous story, just wait for this.
She contacted me.
She was getting sued and she was like, Kelly, I don't understand what's going on.
Can you let me know?
And she did one of those loophole giveaways where, oh, tag, you know, six of your girlfriends follow them.
And you follow them and we'll give you a bag.
So she did one of those.
There was this guy who followed all of those six girls.
And it started a massive fight with him and his girlfriend.
and because he just followed essentially six new hot chicks.
Oh, my God.
And I guess they broke up.
They had issues.
I don't necessarily know the details on it.
But he was trying to sue her for nominal damages, aka $6, I think it was.
Stop this.
Yeah, yeah.
For like, I forget what it was.
I think I have the contract, but like defamation or something crazy.
And she was like, what is this?
And I looked at the case and I started dying laughing.
I was like, listen, you don't have like that much to worry about.
This guy just seems a little bit crazy.
Yeah.
But he literally was suing all of.
was like six girls for six dollars.
So you were getting sued?
Not me,
not me.
One of the girls from our season.
Oh,
one of the girls from your season was getting sued because she did a giveaway because
this guy broke up with his girlfriend because of the giveaway.
Because he followed,
yeah,
he followed all of these girls.
And then the girlfriend broke up with him for following them.
Yeah,
it was nuts.
I do think that,
I mean,
totally off topic.
I think a lot of those giveaways are going to get crushed.
Yeah.
Because there's not much compliance with them.
Yeah.
It's like,
away, and there's not like the, you know, I mean, you would know this better than me,
but all the legal bullshit with giveaways, and we're going to make sure it's equitable.
Like, I don't know about, like, I think that's going to happen.
There's, like, different kind of giveaways.
I've done, I've done, like, a couple of them, and they were, like, really fun to do
because we would, like, go buy a girl, Louis Vuitton, and, like, it would just give you
exposure to another girl, and then, like, if they liked you, they would continue to follow
you if they didn't drop off, you know, like, it doesn't hurt anyone.
But, yeah, it was, it was quite crazy.
This wasn't for a company.
This was more of just go follow.
my six girlfriends.
This wasn't like, hey, I'm giving away this for a company and, like, all those rules
and regulations were there.
It was just go follow my six girlfriends who are also influencers.
So someone from Peter's season, we'll try and in the recap, we're going to guess.
I'll say, I can say the name.
I'll text her and see if she'll text her.
If not, in the recap, we're going to take a shot.
Who got sued from Peter's season regarding a giveaway?
I think there's going to be more of those lawsuits coming.
I mean, it's a crazy world.
All right.
I got to ask you this.
professionally. You're a nomad. You're all over the place. Chicago, Miami. You got Peter in New York. Where is
Kelly Flanagan going to live now that your work is flexible and your relationship status has changed?
It's a tough one. I love Miami, but it's not feasible for Peter. So, yeah, it's been tough.
I mean, I've always been okay with New York. I think New York is amazing, but, you know, it's something him and I have to talk about.
Figure out where you want to go and stuff.
I don't think L.A. is necessarily my scene.
I could see myself in New York way more than any of the other cities that, you know, he has access to or United has a base.
So I don't know.
We're not necessarily there.
We have some conversations when that does happen.
Figure that stuff out.
That stuff will come.
And so will, what's next for you.
I do want to talk about the Lyme disease.
So back in 2021, you're diagnosed with Lyme disease.
He started this podcast off saying you were.
shot and you attributed it. It could be Lyme disease. Yeah. It most likely is. I just sometimes
like get annoyed with it so much and I almost like to pretend I don't have it and that sounds so bad.
Yeah. But like I don't like to like be negative in that sense. So when I'm like feeling bad like I don't
want to like I almost just try to like push through. Yeah. But also I think the cool thing about what
you've done and it's even tied to your professional influencing career because I think a lot of people
are gravitating towards it and you're making an impact is like you are an advocate for Lyme disease.
I had no idea about the severity of Lyme disease until I was honestly educated by you.
And I think there was a lot of people out there that fall under that boat.
I mean, what can you tell us about the diagnosis and what is like the status of how you're working on everything?
You know what?
There was for nine months.
I was on like an extremely strict diet.
I was doing like a lot of, I don't even know where to start, but I was on extremely strict diet where I was only essentially allowed to eat meat and vegetables.
like no drinking no sugar no fruit like absolutely nothing like you can't mess up for one day type of thing
and then i had like a bunch of red light lasers where i would have to like go all over my body
and like stick them in certain places to a help it helps with detoxing and then i had like this
plate that shakes and stuff like that and then i would have to hear like light therapy and like
noise therapy and all this stuff and i think that it worked so well for my brother the the problem is
I think that I was taking like so many supplements.
So they give you just like these bottles and you have to take them like, I don't know,
25 times a day.
I think that something in one of those bottles was still inflaming me because I was gaining.
I was gaining so much weight.
I was inflamed.
Like you could just tell my body.
Like I was, I'm probably like 20 pounds up from what I was like maybe last year.
And I was like, why?
You know what I mean?
Like, why did that happen?
And that was within the nine months of me eating.
the cleanest I possibly could. Yeah. So I was like, this doesn't make sense. Yeah. So I think that
like something within those bottles that I was taking, again, like if I'm allergic to it and I'm taking
it three times a day, like imagine. It mess me up. So I stopped it because I was like, this is not
making me feel better. Now I think I'm just at a point where like I know how to eat healthy. I've
taught myself so well to take like these little steps. Like the amount of massages I get Jason is
absolutely insane and it's not necessarily because like I want a massage like the first thing to go when
with my lime is like my muscles and my neck and shoulders they just like tense up and it they
just like kill me like they just hurt like it's out of nowhere like again if I'm eating gluten
or something that like triggers it like it just like hurts like it hurts and it's like just hard
and then there's a bunch of other things that come with it but yeah it's tough and I just try to
stay as healthy as I can. And this literally comes from a tick bite. Yeah. And you have no idea.
Like, you can't track this stuff, right? No, agreed. And I grew up in the woods in Illinois, but also,
I think that you can pass it down. You know, there's studies that say you can. There's studies that say you
can. There's studies that say Lyme disease doesn't even exist. So at this point, like, just do your research
and see what applies to you. But no, I think that you can pass it down. And that's like something that
scares me even more to like have kids and like have to worry about that stuff. But yeah, I don't
know if I got it when I was younger. I don't know if like my mom had it, but, you know, because
there's three of us in my family that have it. Like think about that. Yeah. Like what are the chances
of that. All right. For anyone that's listening and they want to learn more about Lyme disease or they
want to find a way to get involved with Lyme disease and give back, what would you recommend and where
would you tell them to go? So I actually work with a company. I reached out to them and they're called
hygienics and they're like the testing for Lyme disease.
So, and what sucks is the majority of tests for Lyme disease are so inaccurate.
Damn.
Yeah.
And the government also says that Lyme disease doesn't exist.
So it's not covered by insurance.
So nothing is covered by insurance.
Soigenics right now in the market is the best test to take in terms of accuracy.
And then I work with Global Lime Alliance, which is a great company.
They're like doing so much research.
We just went to their gala here last week.
think they raised like $1.885 million or something crazy like that. So that makes me super excited.
But they just have a lot of knowledge behind it. And it's crazy. Like they were telling me I have a lot of Zoom calls with them and I talk to them a lot. And because they know I have a platform and I try to share as much as I can to help them out just to bring awareness. And it's just crazy like how people, you know, you could be totally fine. Like there is a Broadway. I think her name's Ashley. I can remember. She was one of the Broadway girls.
But she came on and she said her entire life, I think she's had Lyme for several years.
She's fine.
Like you wouldn't know.
And then just one day it was triggered.
So some people are just not impacted at all.
And then some people it turns their life for them.
Yeah, because it can go like, it's not always active.
Like it could just be dormant.
And then if you're like going on benders or drinking a lot or not taking care of your body,
then it could like come out and you're screwed.
But she came on and just said like just one day I picked up.
And then, you know, having Zoom calls with them, even the vaccines and how people were going
and getting vaccines, and their Lyme wasn't active for 20 years,
and all of a sudden they're, like, shot, like completely shot.
So it's little nuts.
You don't necessarily know how it's triggered, but, yeah, it's a bunch of different ways.
It's a crazy, crazy, crazy disease.
And I did some research on Lyme disease cases rose 44% between 2010-2020,
and 14% of the world populations may have had Lyme disease.
And then they also said, I think this is interesting.
75% of people who've contracted it will develop a rash on site.
So not all people do.
No.
It goes undiagnosed.
But some people do.
I mean, it's crazy stuff.
And also what's crazy about those numbers, too, is I think actually a lot more people
have Lyme disease than they know.
But again, the government, like, who's going and getting tested for Lyme?
But I think this is a more common thing where people, like, have autoimmune issues.
And they're like, okay, now what do I do?
You know, Lyme is more acknowledged now than it ever was.
So I think a lot of people have Lyme, but it was just never acknowledged.
It was never acknowledged.
I think that so many people have Lyme and they just, they don't know.
And so where can they get tested with the group they work with?
Hygienics.
Guys, check it out, especially if you're, I don't know, if there's any concern at all.
Like, why not get the information?
All right, Kelly, let's end with this.
We're doing a rapid fire here.
It's from the Money Mafia.
Those are the people listening to the show.
We're going to do a quick rapid fire, and then we're going to wrap up with your trading secret.
Okay, ready for it?
First one, best deal you ever got on Instagram.
My manager is here.
Help me, Evan.
Best deal you ever got her?
Restlein.
Restlein Botox.
No, no, wrestling filler.
Oh, like lip filler.
Yeah, yeah, yeah.
Okay, there you go.
And it's funny because, like, I, it's so funny because my entire life, my face has always just been, like, round.
Okay, so when I was going with one of my girlfriends, Kelsey, and I was like, no, I don't want filler.
I would always be afraid to get filler because I was like, I don't need more volume in my face.
Like, this shit is already intense.
So when I went there, and again, I haven't gotten it done, I want to go get it done again.
But what they do is like, I'm so cheeky right here, like in the front, the apples.
So what they do is they actually can like slim my face.
So they put the filler like in the back, like kind of more by your temples.
And so it like pulls it back and it just like makes it less voluminous here.
So people will always be like.
oh my god she got too much filler and it's like no no no they could actually shape your face
to not make it so voluminous because mine is already like I have so much volume in my face to
begin with a hell of a partnership pays well yeah does you well yeah I love the explanation
break down but I used to be so scared now I'm like oh god you're like bring it on yeah let's go
all right worst deal worst deal you ever agreed to what can you think of I think there was like a
giveaway that you know with me like right now I barely have any makeup on I just sometimes we'll get
super dressed up. And like other times I just don't care in this giveaway, like, wanted me to
like dress and look a certain way. And it was just like the way they were going about it to like
kind of try to look prestigious. And I was like, that's just not me 100%. It just like rubbed me so
wrong. Yeah. Being like, no, she has to go put on makeup. She has to. And I was like,
no. So they're giving you these requirements that you typically in a day to day don't fulfill.
Yeah. And it was not me. Yeah. It was definitely a weird one. Okay. That's good. All right, investment
option. You got one opportunity to invest
in anything right now. What would you? It could be
anything. What would you invest in? There's
no wrong answer.
I mean
my most recent investment
I did a real estate investment fund
which was cool.
And then actually my most recent one
was RX3. It's Aaron Rogers Fund.
They have a bunch of partnerships
I'm going to start working with here.
Theragon is a really cool one. They do
core power yoga stuff like that.
Awesome. All right. Stay tuned to the recap. We'll talk all about
that are fun and what they do.
Instagram influencer or lawyer.
You got to pick one.
What are you picking?
Influencing.
Chicago or Miami.
Miami.
New York or Miami.
Don't ask me that one.
Probably Miami right now.
TBD.
Peter's listening, so she's not going to say,
Bachelor or Bachelor.
Like which one do I like watching more?
Which you prefer, yeah.
Probably Bachelor.
Bachelor or Bachelor in Paradise?
Probably Bachelor.
Would you ever go or do anything associated with the franchise again if they wanted
have you on a spin-off or maybe even do your wedding if that's what happened oh man you know i don't
ever regret going on the show i don't think i have any animosity towards them i don't think they
have any animosity towards me but i don't think like i'm going to live my life around them you know
am i open to something if it like benefits me in a cool way and it like sounds exciting sure
doors open yeah all right in 20 years from now do you think you'll be which one of these two
a CEO or owning your entire business i would say owning all right
That's all I got. That's the Money Mafia rapid fire with Kelly Flanagan.
Kelly, before we can conclude this episode, we got to get your trading secret, something people
out there can learn from you, money management, financial management, life navigation,
career navigation, anything goes, it's your trading secret. Kelly Flanagan, what can you leave us with?
I would literally say if you guys want to be successful, what I have learned is making and keeping
and establishing connections is one of the most important things you could ever do. It's crazy
the amount of opportunities I've been given just because I've made a friend and they've wanted to
help me out and the amount of friends I help out too. But I think connections are one of the most
important things that in order to be successful you have to have. That is a hell, a hell of a
training secret. And it's so true. One relationship, one handshake.
One interaction can change your entire life.
And not only that, I know people love to stay behind their computers and their phones.
There is no substitute to in person.
There's just not.
If you look at every statistic out there about how quick something can accelerate, whether you're dating, whether you're looking for a business partnership or your next opportunity, if you see those people in person, it's going to accelerate it big time.
Kelly Flanagan, thank you so much for joining us on Trading Secrets.
Guys, stay tuned for the recap.
We're going to talk about some of the statistics out there with the attorney field, the percentage of women, percentage of men, what law school looks like, the cost, median pay, et cetera.
So stay tuned to the recap.
And Kelly Flanagan, thank you so much for joining us.
Where can people find everything you have going on?
On Instagram, Kelly Flanagan, just at Kelly Flanagan, but I have an extra E in there.
Extra E and TikTok.
Your TikTok's blowing up, too.
I know Evan would want me to mention that because he wants more deals for you.
Guys, thank you for tune to another episode of Trading Secrets.
one you can't afford to miss.
Ding, ding, ding!
We are ringing in the closing bell to the Kelly Flanagan episode.
David, I know you're a huge fan of hers.
You were just with her in New York.
I mean, she called you amazing, but there are so many curiosities that I am sure
have got to be driving you crazy here, from the school tuition, to the fact that dad paid
for all those, the family business, the whole bachelor side of things, in the career after
the bachelor, and then, of course, obviously, the relationship with Peter.
So where do you even want to start with this recap?
The curious Canadians antenna's got to be going haywire.
Well, anyone who calls me amazing is just buttering me up for a nice, solid, a five-star recap.
So thank you, Kelly, for coming on.
Thank you for calling me amazing.
I had the opportunity to meet her and Pete for the first time together at a Kygo concert
a couple weeks ago on the day that I told Evan and Ben that Asher was pregnant,
so they were a part of that.
Amazing, amazing couple.
All right, we're going off the record here, business idea.
How about like personal side?
Did they party hard, drink hard? Hey, like, what's the vibe like?
The vibe was chill. I mean, it was a Kigo concert, really quick on the Kigo concert.
It was at MSG. I've never been to a concert in a building where everyone was so happy
because Kigo plays the happiest music. And it was just like meeting them for the first time
at that concert together at a big moment, Ashley and I's life. They were awesome, awesome.
We went to dinner before. It was, it was a good time. Great people, happy that she came on.
I want to put this out there real quick because you had just met them. And they left,
They experienced a big moment with you when you shared that your wife is pregnant.
I want to make sure everyone out there knows.
Kelly obviously comes from a family of wealth.
Peter does very well and was the bachelor.
They are both such down to earth, humble people when you are sitting there one on one with them at a dinner.
You would never know any of the background of any sort.
They're so real and I really want to make that crystal clear.
Here's how I can accentuate that.
Me and Pete are still in a group chat talking football, Sundays, Seahawks, nonstop.
We went up for dinner for Evans' birthday the night after I got to spend more time with them.
Kelly flew back.
And here's something to old Kelly.
She didn't have to do this.
Very small gesture in the world we live in.
She followed me back and she followed my wife back on Instagram.
Actually, I think she might have followed my wife before.
My wife even followed her.
But just like super cared, genuine, like she was awesome.
They're awesome.
If there's any Pete and Kelly, naysayers out there, stop it.
They're a great, great couple.
They're great together.
It was great to meet both of them.
So awesome to have her on the podcast.
But favorite episode, favorite part of the episode, similar to the Joe episode, when you
have these bachelor personalities on true trading secrets fashion, trading secrets about
their life, how they got there, their upbringing, learning more about them.
So that was my biggest takeaway.
But I think I want to start with the school, man.
You seem blown away by it, by the idea of it.
So I want to see if that's still like affecting you.
Is it still popping in your head when it's a random Thursday afternoon.
thinking about how boarding school, Culver.
I'm just trying, David, here's where I'm going with this.
And the viewers out there, by the way, right now I'm calling the viewers the Money Mafia.
If it sticks, it sticks.
If it doesn't stick, it doesn't stick.
If you guys like the Money Mafia, go give us five stars and give us the approval.
Then we've got to give the $100 out to the individual that helped us with that name.
But the biggest thing for me, David, is I've had some decent success at a young age, got a couple bucks saved away.
I could never imagine spending 35K a year for my kid to go to boarding school.
Maybe it's because I don't understand it.
Now, you coach at Bishop Carney, and my understanding, correct me if I'm wrong,
but like it could cost up, there's obviously a lot of moving parts,
but it could cost up to like 60K a year for a kid to play hockey at prep school at Bishop Carney.
how does one ever justify that help me so here's what i'll say to that you know ours is a
financial aid based program a 59 000 a full pay so we have a a variety of what people pay i'd say
the average is mid 30s so similar to what kelly was paying to culver what i will say is this the people
who are full pay at our program end up being our happiest customers and you might think why right
if there's someone paying 59 it's because the people who are paying full pay are successful
business people and their careers in the fields, they understand value. They understand hard work.
They understand dedication. They understand commitment. They are always the happiest because they see
the value in the product that they're sending their son to. And so they're always the happiest,
whereas people who, you know, are here on financial aid might not understand the level of work
and value that they're actually receiving. And so sometimes they're wanting more, even though
they're paying way less. They're not understanding of everything that really goes into it. You know,
it's all about opportunity. One of the best parts of the episode that she talked about was her
parents upbringing and how different it was from the life that they're living. And obviously
somewhere along the way to probably spend what is, you know, quick math calculation,
six siblings, culvert, grad school and undergrad degree somewhere around $3 million. He feels
the value in the education of sending them for this experience to learn the life lessons.
And Kelly admitted 14 year old brat. Kelly needed it. She was throwing a hissy fit about,
you know, having to make her bed or not being able to call her boyfriend or something like
that at the time. So I think money well spent, seems like a pretty great family. I give them credit.
I mean, you think about the dollars and cents, five kids. What, you know, you know,
if you 40K a year, let's call it, 160K, 5 kids, that's, you know, 800K. Then you got law school
and undergraduate. That's another easy, easy 800K. You're talking 2 million plus. And what I
always like to tell people, the biggest tip I could give them is when you're thinking about spending,
when someone says, I spend this much on instantly, just for safety, measure at times 1.5.
because that's the gross income you need to actually spend that, right? So if he generates
$3 million in gross income, that gives him, let's just say, $2 million of spending power. That
$2 million of spending power probably went to all the schools of all the kids. And I guess
that's like a dream. Like you could put, you talk about like legacy. We just had Miguel
Cervantes on. You think about like the end of your day, you've been so successful. You've
been able to grind a business to put five kids through law school and change the entirety of their
trajectory. That's amazing. Yeah, and shout out to BK. We went down to Culver and played them
in hockey last year and smacked them two games. Beautiful campus, though. Me and you,
it was like, it is truly middle of nowhere, Indiana, but it's on a lake, has a golf course.
It's beautiful there. But after saying those numbers, I feel like it has to be justified
after all the investment that the dad's put into it. Did you ever have an opportunity to work
for a family business? Do you get the family? What's your opinion on the family business model for
for people generation after generation, taking less for meaning more kind of thing?
Yeah, I think like when it's, when I've got to work with family businesses, especially
on the banking side. And there's so much pride that is so much greater than the salary.
It's not about the dollars and cents. It's about the legacy. It's about the generation
passing on to on. But man, there are some headaches in family businesses. Ego starts
to get in the way and, you know, brothers, one brother's doing really well on side hustle outside of
the business and the other sister sees that and there's envy in that and there are just so many
tangled webs in family businesses so I give so much credit to those businesses that have gone
generation to generation but I want everyone out there to know just like I say it it is so much
harder than what you see from the outside especially when you see these massive changes in culture
and communication and how generation to generation think about what we do now with social media
it creates a lot of disparity in what previous generations thought, you know, was the case. So it's
harder than people think. I also see it being hard too. Like, okay, you invested all this to get them
there, to give them that salary. Yes, it's lower than the norm for the industry, but it comes
with the school, the education, the cell phone bill, the gas card, all that stuff. That's all good
and dandy. But now you're a functioning adult. Now you're in a relationship. Now you might need
to move in with someone. I didn't even pay rent. It's hard to, you know, yes, thank you. You set me up
to get here, but this isn't realistic moving forward. So that's kind of always a give and take there.
One thing that I did love, and I'm sure when you heard it, you were just like smile ear to ear.
Every penny she's made from Brandeel, she's invested. So that's like a Jason Tarduk, like two
thumbs up, pat on the back, like money off you type stuff. I was like that is such a luxury.
I love it. I think it's the coolest thing. It's kind of opposite for me, especially when I was
double dipping with my banking job, I, with the second I got off the show, about a month
after that when I started taking deals, from that point on, I never spent one penny of my
banking salary. It all went in new account. Didn't touch it. Every by week, it's coming in,
coming in, bonuses come in, never spent a penny. And it made me realize, holy shit, a year
or so of not spending a money, I obviously have money saved up, but like,
How do you build wealth off that?
That's part of the reason I'm thinking about this second book, like building wealth as a W2.
Because if I didn't spend a fucking penny, which is impossible for anyone to do.
And at the time, I had a $165,000 salary with bonus structure and a nice expense account.
And I look at the end of the day of like what's left.
I'm like, what?
Not spending one penny.
It is so hard to build like legitimate savings and wealth in this world.
It really is.
terrifies me every day. I mean, you know, I had the same salary for a job where I wasn't paying
rent, wasn't paying utilities, wasn't paying for food. I moved back to Rochester, bought a house,
got married, kid on the way, have a quote unquote dream job, make a quarter of the salary that
I was there. And trying to stuff $100 under the mattress or put $100 in a 401k, it's really hard.
So now she's obviously pretty committed to the influencing thing until she's not. How long do you
think she's got a career in that? Do you think she's an influencer lifer? Do you think that she's
going to get bored or find a new passion? The one thing I'd like to see within her, because she does
great. And I know this, right, because we run the agency, she does great. And I know she takes deals
outside. So I'm proud of her for that. But I'd love to see her really step into what it's going
to be for Kelly. Like, is it going to be the fashion side? Is it going to be, I'm the badass attorney
and I'm going to help women in professional careers with, you know, high concentration of men.
Is it going to be, like, I'll give you, like, expert advice on tax stuff?
Like, I don't know what it is, but I think if Kelly were to step into something, own it,
create stuff around it, it could be next level for her.
But that's what she would have to do.
It can't just be go travel and this is where I go because it's not, it's not sustainable.
And quite frankly, with some of the places she gets to go at the level she gets to do,
at the level she gets to go, it's not economical or scalable for her viewing audience.
I feel like it's also not on brand. I feel like she knows almost to like when she went on
the bachelor, not that she's above it, but she knows that like she doesn't need the bachelor.
She doesn't need influencing. She has a law background. She has a family law firm.
I think what she talked about like the legality of influencers is a really unique niche for her to be in.
I have to ask it because you said it in the episode, RX3. It's a Aaron Rogers fund that she mentioned
that is something that she's invested in. Can you just touch on what that is real quick? And then we can
wrap up. Yeah. So it's genius. Like what Aaron Rogers did is he got a bunch of really smart people
behind him. They used his name in these smart people to then go have people invest in this fund,
people with notoriety. And then they take this fund and they go invest in businesses. And they get
to tell some of these founders, like, we got Aaron Rogers. We have this celebrity. We have this
celebrity. And Kelly was part of that group, and I actually met with them, talk about investing
into them. And I think what they're doing is great. It wasn't the right fit for me, but what
they're doing is great. And they're leveraging the power of people's name and influence to help
raise capital to then help deploy the capital to businesses that want those people involved, right?
So imagine you have a startup business. It's a sports energy drink. And some guy who's extremely
smart and venture capital says, hey, I have a fund, and not only do I have a fund, but Aaron
Roger's behind it, and that actor's behind it, and this musician's behind it, and those reality
stars are behind it. It's a brilliant concept. It's one, maybe one day I'd love to replicate,
and it's a really good move on her part. To be aligned with those people and be investing
that fund's a good move for her. Love it. Well, speaking of investing and hearing Kelly's
story and all the money her dad had to spend on his kids schooling, I might need to put you on a
task. I might need you to educate me on setting up a school fund for my soon-to-be child so that when
they're ready to go to school, I can actually afford it. So I'm going to task you with that.
Maybe we'll touch on it to the boot camp, the February boot camp that I hope is still planning
for in Nashville in February. I would love to touch on that. But overall, great episode.
Thank you very much, Kelly, for coming on. Long overdue. But it was a good one.
Kelly, Peter, congratulations. We are so happy for you guys. If you are going into 2023 and you are
looking to better your health and build your wealth, we are going to have a trading secrets
boot camp. It's going to be February. It's going to be in Nashville, Tennessee. And if you're
interested, just shoot us an email. It's just going to be Jason at rewiredtallant.com. And we will
make sure that you are on the waiting list for that. We're going to have a very select number of seats
there. So, David, thanks for bringing that up. If you like Money Mafia, go give us five stars in the
ratings and give us affirmation. We need to know. Also, we do have three people picked out.
We will announce those people on Instagram for who will win Miguel's golf item.
We bought a bunch of those.
So that's coming to.
And David, I'm going to give you a little preview next recap about some ideas for saving for children as you're preparing for their next steps in education.
There's a lot of tax benefits associated with that.
So thank you for tuning into another episode of Trading Secrets.
Hopefully this was one you can't afford to miss.
And we will see you next Monday.
Making that money, money, playing on me.
Making that money and money, living that dream.
Making that money, money, money, pain on me.
Making that money.
Living that dream.
Please note that this episode may contain paid endorsements