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September 13, 2022 56 mins
Serial entrepreneur & sports agent AJ Vaynerchuk joins this episode of The Bag! AJ, Lindsay, & Rashad discuss the evolving crypto-market and how it is impacting the sports world, as well as Vaynerchuk’s new NFT beverage partnership with Russell Wilson, and how AJ became an early investor in Uber (and the first ever Uber rider!). After years of being an executive at Vayner Media, AJ brings next level business savvy and a media mindset to the sports world, and it is no surprise that his agency Vayner Sports is now poised to become one of the most important forces in the world of sports business & athlete management. Come check out the discussion on The Bag! See omnystudio.com/listener for privacy information.
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Episode Transcript

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Speaker 1 (00:00):
Never No, Never good big. Hey guys, welcome to another
episode of Sports Illustrated and I Heart Radio is The

(00:21):
Bag with me Lindsay McCormick and my co host Rashan Jennings.
The Bag sits at the intersection of sports and business,
delving into the headlines and behind the scenes of athletes, entrepreneurship,
and enterprise Rashad. Today we're sharing a great guest with Everyone,
sports agent, CEO of Yer Sports, and the first ever
Uber writer, A J. Vayner Chuk. Thank you so much,

(00:43):
A J. For taking the time to speak to us.
We have so much to to unwrap with you. The
first question I had though, is have you ever had
a job that you weren't the founder of? Yeah? I have. UM.
My first real old job was at my father's wine shop,

(01:06):
just kind of typical, um, you know, teach you work
ethic type stuff, stocking shelves, moving product around, you know,
helping move boxes, just work ethnic type stuff. But even
that that was from my father. My only job that
I wasn't a founder of and wasn't um and it
wasn't like a family business was I worked at a

(01:28):
local supermarket my junior year of high school. It was
a supermarket called A and p UM. I don't know
how regional it is, but I grew up in Jersey,
and yeah, I was a cashier and bagger at a
grocery store my junior of high school. And then from
bagging groceries where you worked for your family's company, and

(01:49):
then you guys started Vainer Media and you started investing,
and then from Vainer Media you took a sabbatical, and
then from the sabbatical you started Vainer Sports. Correct, So
to kind of give the cliff notes, how so during
the sabbatical, what sparked the idea of Vader Sports. Yeah,

(02:13):
so you mentioned um, I was lucky enough to be
in a position where I was investing in companies at
a pretty young age simultaneously to running the ad agency,
and did some angel investing my brother and I, and
that success led to starting a fund. So we had
a fund um And so by the time when I

(02:35):
left the ad agency about six years ago, between my
personal investment portfolio and our funds portfolio, probably had about
a hundred companies I was associated with. And so when
I took the sabbatical, you know, the first month or so,
it was a clean break, like I wasn't checking email,

(02:57):
I wasn't taking meetings or phone calls. A lot of
people asking I was just like, listen, I just need
to like really go off the grid for a minute.
And you know, I just basically played golf and walked
my dog and hung out with my um my wife
was my girlfriend at the time or fiance at the time,
and um. But then after about a month, I started

(03:18):
kind of just passively looking at portfolio companies and catching
up with them. And uh, shortly before I left, we
had Gary and I had invested in a boutique sports
agency that represented I think three or four NFL players
at the time. And you know, two to three months
into my sabbatical, I initially planned to take a year off.

(03:40):
Two to three months in I really got interested in
the day to day business of representing football players. And
I found myself talking to my current business partner, Brian.
He was the founder of that sports agency. We ended
up acquiring it and rebranding it. But I just was
talking to him more than anybody else in the portfolio,
and it kind of made it. It just crystallized that,

(04:03):
you know, this was a passion for me. UM. I
grew up a diehard sports fan I UM, and I
felt that both my business background and client services because
you know, servicing Fortune five d cmos and CEOs can
be very similar to servicing a professional athlete. And then
also you know, from the the investing side, UM just

(04:26):
started running into a lot of athletes prior to starting
the sports agency. So guys like Carmelo, Anthony, C J. McCollum, Dominquin,
Sue Um. These were athletes that were actively investing in
early stage tech like my brother and I were. And
so just breaking bread with those guys help me see
a gap in the marketplace when it came to athlete representation.

(04:48):
I love it so uh kind of switching gears a
little bit. The beginning stages of any company, any business
and adventure, there's always the the first to market, the
first to do, the first to try. UM And so
a few little humble brags that I have and I
can hold for the rest of my life, one of

(05:09):
them being the Dallas Cowboys. That beautiful billion dollars stadium
that they have is is luxurious. If if nobody, if
you're ever in tactas you get an opportunity to stop
about check it out. It's worth the tour. I actually
went on the tour um as well. So one thing
about that stadium, the very first game ever played inside
of that stadium was the Giants versus the Cowboys. The

(05:32):
very first teams that ever win in that stadium was
the Giants. So forever as forever as that stadium exists,
as I always have one up on a Cowboys fan
to let them know, you know what, we own that stadium.
And we carved our initials in the locker room just
so you know, UM it's and and so many other things, right,

(05:52):
like just just the first And so I heard that
you kind of have a similar situation to a company
where you were the first of its kind and at Uber.
So I would love for you to tell us about
that and how you got involved with Uber. Yeah, no,
I appreciate that, and thanks for teaking that up. So
um Uber was one of the first companies I got

(06:15):
to privately invest in. This is in two thousand and ten,
um second year of the adding. You see. So I'm
twenty three at the time UM, and I think Uber
was my maybe my third or fourth investment I ever did.
And uh, what was really fortunate for me was that

(06:37):
I had a relationship prior to Uber's existence with both
of the co founders. So Travis Kalinik, one of the
co founders who eventually went in and jumped into the
saddles CEO and ran it for quite some time, and
then also Garrett camp so knew both of the co founders,
was closer with Travis, and uh, when we invested um,

(06:58):
Travis actually did me a real solid Uh. You know,
I didn't have the type of capital that was required
for the minimum investment into the round, and Travis actually
made an exception and let me invest a smaller chunk
of change, and so that was really dope him. Um So, yeah,
invested in Uber. And the fun fact that you're referring
to the one that I'm excited about to share with

(07:19):
my kids and my grandkids is that um so uber
started in San Francisco and the first people to ever
ride Uber where Travis and Garrett, obviously they came up
with the idea. They started off with a single car
hooked up to their iPhones, requested it and wrote in it.
And then their second city that they ever launched was
New York City. And when they launched New York, Travis

(07:42):
called me up and said, hey, um, we're just about
ready to go live in New York. Can you be
the first person ever ride? Are you available right now?
I said yeah, I mean I've got I've got thirty
minutes until my next meeting. He said, listen, I literally
just need you to request the car, get in the car.
It'll do a circle around the block our offices in Manhattan.

(08:02):
And so I literally pulled up Uber and the first
message said, you know, the cliche message of hey, we're
not in your neighborhood yet. If you want Uber in
your city, like request here. So it wasn't live, and
then I closed the app and I reopened it and
there was a single car, so all in Manhattan, and
there was a single car showing up and that's used
to when you can see the map. And so I

(08:23):
requested and the car came through. I walked out my office,
I got in. We I'll never forget it. We went
down twenty three, we made a right on second half,
we made a right, then we made another right back
up to third half, and they made it right back
on and I literally just did a circle. Um. And
so I was the first ever person to ride in
Uber in New York City. So fun little fact that

(08:44):
I get to share. That's awesome not only just a
first ride in New York City too, exactly pretty you know.
I think about it and I always say, like, I
couldn't imagine if like one of my grandparents took the
first ever yellow taxi in New York or the first
ever subway ride in New York. So pretty pretty cool
thing I get to Yeah, I always say that's awesome.

(09:04):
And another first, I believe, Um, you know that you've
been a part of our players contracts. I believe Kirk
Cousins was one of the first fully guaranteed contracts in
the NFL, and that's something that we've discussed before, Lindsey.
Um is about players getting to the position where they
can get fully guaranteed contracts because pro sports and football specifically,

(09:30):
that's uncommon. And so being a part of that historical contract,
take us through how that negotiation came about it and
YA was able to land. Yeah. I can't speak as
great of detail on that one, because while Kirk is
a Venter Sports client, he's actually a fairly new one. UM.

(09:51):
So all the credit for that contract needs to go
to a gentleman named Mike McCartney, who's now my business partner.
So Mike, uh, longtime football guy, you know, grew up
His father is the legendary Bill McCartney Colorado National Championship team. Uh.
So Mike grew up in football and then uh he played,
and then he coached, and then he scouted for the

(10:13):
Bears and the Eagles, and then he switched to the
agent side about twenty years ago. So Mike's been in
the business a long time. He's accomplished quite a bit. Um.
And yeah, he's been Kirk's agent ever since Kirk got
out of Michigan State, um and entered the draft, has
been in the NFL, and so um, yeah, I can't
you know, my recollection understanding of how that contract negotiation

(10:33):
went down would be the same as any fan, just
because uh, we weren't working together just yet, but yet
having Mike in the fold now and Kirk in the fold,
and if you look at I think how Vader has
done contracts to date. So while we didn't do Kirk
at the time, Um, you know, I just recently did

(10:54):
Foyer Leucon's deal down in Jacksonville, DJ Reid's deal down
in actually in York with the Jets, and then also UM,
my business partner Brandon Parker, he did, uh, Leonard Williams
with the Giants recently, UM Alan Robinson with the Rams
and before that with the Bears. And so if you
look our our agency and generalist, is something that Mike

(11:14):
and I really saw eye to eye on and why
it makes sense for us to be partners now is
really just maximizing that guaranteed percentage and maximizing leverage. And
I think if you look at the contracts that Kirk did, that,
Leonard did that, Foyer did that, DJ did, UM, you'll
see a theme of high percentage of guarantee and always
trying to push that envelope to make sure that that's
you know, a big factor for an NFL contract. When

(11:39):
I look at some of these guaranteed contracts lately with
with all the guaranteed money, and then I look at
the I know you're a business partner with Russell Wilson,
and then I look at the contract he just signed
where it seems like he almost took a pay cut.
What are your thoughts on on that situation? Yeah, you know,
my my business partnership relationship with Russell extends to a

(12:01):
project that we're working together on called Local Weather, which
is a beverage based product with an n f T
layer associated with it. When it comes to Russell's football,
we are not business partners on that end. And so
just out of respect to his agent and other agents
out there in terms of, you know, the deals that
have been done recently at the quarterback position, I'll just
say that, Um, you know, our personal approach is to

(12:26):
um focus greatly on the guaranteed portion of the deal
and to maximize the opportunities to double dip, triple dip,
quadruple dip, etcetera. So we like our contract short and
duration and high in percentage of guarantee. How does that
business partnership come to be and why what makes Local

(12:48):
Weather proprietary? Yeah, so that business partnership came to be
UM from just a mutual relationship with the CEO and
CEO of Local Weather. So there's two great founders behind
the project and somebody that I've known for a while,
and then they also knew Russell for a while, so
they really sat at the center of bringing and bridging
the gap and bringing the two sides together. And as

(13:09):
far as Local Weather goes and what makes it propriety
and what makes it unique, um one, just the ingredients,
but I won't go too deeply into that, and I
think just in general, UM, the market for a better
for you hydration beverages is one that has a lot
of competitors in it. So I won't say, you know,
saying that we have special best ingredients isn't necessarily proprietary,

(13:30):
because I think a lot of functional beverages go that route.
But I will say that that's something that I know
the founding team you know, stands their leg on and
is passionate about. And then I think the other thing
that I mentioned briefly is that in general I have
a fascination between the bridging of physical and digital and
how the blockchain and n f T s can do that.
And so, UM, we do have a n f T

(13:53):
collection that is stemming from the art on the bottle
for local Weather and the artists for local Weather, and
so we have a lot of exciting things plan in
regards to just the intersection of sports and n f
T s and UH and hydration and you know, fun
things planned with Russell, we did a fun thing in
a Major League Baseball game recently. UM, and so yeah,

(14:14):
just a little bit more interactive and leveraging the blockchain
technology to do some different things for it. I got
a question. I got a question. I would love for
you to break this down. You talk about bitcoin and
f T, s uh like the meta space like this.
These are all terms that are brand new to a
lot of people. But you see players seeing NFL players

(14:38):
specifically say Kwon Barkley, Odell Beckham, um Brady and Rogers
receiving part of their salary their NFL salary and bitcoins
and cryptough and one do you think that it's smart
to do for athletes? And then two, how do you
break this down in itself? Like for me from an outsider, right,

(15:01):
it seems like there's a yard sale going on and
they found a way to certify the items being sold
in the yard sale and calling it a n f T.
People are selling any and everything and it's just like
a social status, I feel like, But that's that's coming
from a layman's How is it working inside the intricacies?

(15:24):
So the first part in terms of athletes getting their
salary in bitcoin and doesn't make sense or not, you know,
I think the tricky thing I can't really answer that
question fully because I don't know so many key aspects
of their financial matters personally to help understand who does
it or doesn't it make sense? And I also don't

(15:45):
know what their transaction plan was. So for example, UM,
it's possible that they received the bitcoin and they instantly
liquidated it um and thus the financial change it was
really just some transact fees and it was it was
not it was a non event, and it might have
been done as a publicity stunt um, just to help

(16:06):
position them and brand them in a manner so that
they can be seen and perceived as crypto native. So
I don't know if any of those athletes what they
did with the bitcoin when they got it UM, And
I also don't know their current financial status to understand
what type of risk tolerance they should or shouldn't have,
So it's a little bit tricky. UM. I have you know,

(16:27):
the one thing I will address those I've seen a
bunch of the headlines, you know, because crypto is down
right now and people are saying, oh, this player got
paid in bitcoin and they lost all of it, and
that's not necessarily true. UM. So for example, the way
players get paid their NFL salary now is they get
paid over a thirty six week period starting when the

(16:48):
season starts, so literally starting like next week, and they
get one thirty six of their paycheck. Who when you played,
I think it was seventeen weeks that it was paid
out right, The NFL p A and the players decided
to recently shift DIT so that it gets you get
less per week over a longer period of time, because
I think some players were having some issues budgeting seventeen
weeks of paychecks over a fifty two week year. So

(17:10):
now it's thirty six weeks you get paid. And so
the point that I'm making is that a lot of
people say, oh, this player got their NFL salary and bitcoin,
and you know, in September bitcoin was worth x and
then come you know January it was worth why and
they lost all this money. It's not true. Right as
bitcoin went down, they got paid in correlation to the
price of bitcoin based on what they were due to

(17:32):
be paid. So if bitcoin, let's just say bitcoin dropped
in half and they were supposed to get one bitcoin
that week, well they just got two bitcoin that week
because they were getting paid the bitcoin equivalent in US dollars.
So I just wanted to highlight that because there was
a lot of bad reporting around that, a lot of
people saying like, oh, they lost all this money, but
in general they got paid as the market came and went.

(17:54):
Depends on what they did. If they sold right away,
they they broke. Even if they held and there could
be a spike, they could actually make money. So I
just wanted to address that. And then the other part
you asked about just n f T s and your
yard sale analogy. I think that in general, your your
analogy is pretty fair. I think the n f tea
market went through quite a bubble where any project could

(18:18):
be spun up, it could be doing transactions. There's a
lot of hysterea and a lot of people kind of
in a gold rush type mentality. The last few months
have been a lot quieter. Um prices are down dramatically.
You know, Ethereum, which is the primary n f T
blockchain think of theory, was at like forty bucks of
coin in like the spring. It's down about right now,

(18:40):
so eat this way down. N f T prices in
general way down. But I actually think it's been healthy.
It's a bit of a bit of a cleanse um.
It no longer rewards, low effort, bad projects from selling
to the point that you made And now I think
you know, we're flushing out bad actors and bad projects
and are are kind of consolidating in a healthy manner

(19:03):
that I think will make the market more sustainable in
general and a path forward. Switching pasts a little bit.
How has name, image and likeness changed the sports industry?
And now that you can reach out to some of
these younger guys, uh and have business relationships right away
as opposed to several years ago when you can only
have a personal relationship and then over time hope that

(19:25):
that turned into a business relationship. Do you feel like
you're forced to build a connection with an athlete much faster? UM?
You know, yes and no first part of your question.
I think it's changed it substantially, UM. And I think
it's changed for the better. UM. I think that the
amount of money that was being made in college sports,

(19:45):
that was UM going into everybody's hands except the players
on the court, on the field, UM, was always unjust
and always an unbalanced UM. I like to always point
to Florida Gulf Coast Universe City, and if you look
at Florida Gulf Coast. They had a basketball team that
was nicknamed Dunk City. I think maybe five, six, seven

(20:09):
years ago. Uh you know, Cinderella run. I think they
made the Sweet six team, maybe even the Elite eight,
dunking everywhere, fast paced offense, making a lot of noise.
When you look back to Dunk City, UM, and you
look at what happened in the aftermath, here's what happened.
University enrollment exploded because when you were watching March Madness,
they started showing pictures of Florida Gulf Coasts campus and

(20:31):
you saw the beach, and he saw pools, and you
saw the warm weather. Their enrollment exploded right after that
tournament run. The head coach, UM, I can't remember his
last name. I think his first name is and I
think Andy something, maybe Andy Miller. I forget the head coach,
AFFORDA Gulf Coast got a huge contract to become the
USC out in California heads basketball coach. The players on

(20:54):
Florida Gulf Coast, not a single one of them played
an NBA minute. They all had um. I think the
starting five and six man all had European careers and
they made some money, but not a single NBA minute
I think one or two was in the G League,
but never one played a single NBA minute, and so
the university printed money, the head coach got a huge contract,

(21:16):
and the players saw no benefit from that run, literally none,
Whereas if they were able to have n I L
I think the market opportunities around making that type of
run UM would have been substantial, and so I'm just
glad that it exists. UM for us personally, with Manor sports,
we've had We've enjoyed a lot of really nice success
with it. We actually, um, Rahad you mentioned the first

(21:38):
thing that's a business first, we get to use We
brokered and negotiated the first ever national TV commercial with
a paid college athlete, so we um we represent Lay
the Clemson quarterback, and he appeared in the Dr Pepper
Fansville national TV campaign last year. UM, they're using Bryce
Young this year, so they're making a commitment it. It

(22:00):
seems to use a top notch quarterback every year for
their or at least a top notch athlete for their
campaign because they're one of the biggest spenders in college
football from an advertising perspective. So dj first ever college
athlete in a TV commercial, which he was compensated, so
that was fun. UM. And yeah, then lindsay on the
second party of question, terms of relationship earlier, UM or faster,

(22:23):
you know, I think it's different. I don't know. I
think it's for the better because what ends up happening
and and ra shot, you know you went through this, UM,
I don't know what your experience was like specifically, but
I know what you know, the athletes that we work with,
what their experience was like. And then even you know,
I like asking athletes that end up switching over to
us after they're in the league, and I like asking

(22:45):
them what their college process was like to just to learn,
and it's interesting to me. UM. I think now for
a college athlete, they're exposed to business earlier. They're exposed
to UM, what it takes to bo once business of
football at the same time, and they get exposed to
what it's like to work with people. So not to

(23:06):
say that every athlete that works with a agency ends
up signing with that agency for the pros, because we
got to see it last year. Plenty of players ended
up switching and did not work with their n I
O representation when they went pro, but a lot worked
with the same people that they worked with in college
at the NFL level, And I think what's great about
is it gives the athlete and their family the opportunity

(23:27):
to actually see what these people are like when there's
actually work to be done as opposed to just conversations.
Because prior to NIO existing, you know, athletes had to
make a decision for the most part on just what
they feel as opposed to what they see. So I
think that's a good thing. You touched on something open

(23:47):
at Canna worms trying not to focus the conversation down
this lane. But you know, I've mentioned before that athletes
are getting smarter. Therefore the league, the NFL has forced
smart athletes. You have to have a two point through
gp A in high school two point five to stay
on a collegiate team, and so education and introduced to

(24:07):
more n I l so many things, so many opportunities
where when I was playing, and you know, it's still
almost less. It's less than a decade ago it was
frowned upon to do other business ventures while you were
playing football. Now it's almost why aren't you? And so
everybody is encouraged because of it, and so I'm I'm
excited for the athlete. UM, because I was the guy

(24:30):
that was in meetings. I understand this game inside and
now I'm probably helping some of my coaches out, uh
with breaking down film and so sometimes I have too
much time setting in training camp. I helped the rookies out.
I know my game inside and out. What am I
going to do setting here in the meeting for two
hours watching the same little people run around on the screen.

(24:52):
So I was set on the right business plans and
right that would have been frowned upon right now probably
it's like, okay, as long as you hand to lend
your business on the field, why not work on yourself.
So I'm excited about that. With that, With that being said,
tradition UM or traditional things I applaud and I think
we learn from tradition and we grow from tradition and

(25:14):
we make new ones along the way. One thing that
I think I've heard you said, and I don't want
to misquote you, that's what I want you to speak
to it if you can, UM, is you know, coming
into and this is kind of almost motivating people coming
into a new business, a new scene, and you're young.
One of the things that I would say people parple

(25:38):
and is you don't have the experience. You haven't had
fifteen years of experience of doing contract, you haven't had
twenty years of dealing with particular athletes, or you haven't
invested for more than thirty years. So you don't know
as much as I do. And a lot of times
you know this more than I do. Uh. People can

(25:59):
use that strategy to build their clientele by keep on
harpening on experience and and and it shines, it shuns
away the younger experience, right, whatever that sounds and looks like.
I love for you to speak to being younger coming
into a business that is older, how do you succeed? No,

(26:22):
it's a great question, and I've really had to do
it twice um, first with the ad agency and then
second with the sports agency. I think for um, that
is certainly something that I faced throughout my whole career
because I was always somebody that was young in a
position that was I guess further along than my age, right.

(26:43):
So like, for example, when I was twenty five, I
was a chief operating officer of an ad agency with
four employees. And so I think a lot of people
from the outside, whether it's clients that are older, or
potential employees that are older, because you know, when I
was at that point imployees, I probably have like fifteen

(27:05):
people directly reporting to me and all fifteen or older
than me and have more experienced than me. So that's
always been an interesting dichotomy. Um, and just an environment
and energy that I had to face. And I think, um,
I think it's a mix of two things. One, if
you're gonna be younger and less experienced, Um, I believe

(27:26):
it doesn't fit everybody, but it's my belief that you're
going to need innovation and disruption to supplement the lack
of experience so to speak. Right, Like, so if you're
if you're younger and less experienced than your peers, you
can't just go and do exactly what they're doing, is
my perspective. Right, if you're just doing the same thing

(27:48):
that everybody else is doing, I think the easy question
to come to is, well, why would I do the
same thing with you versus the same thing with somebody
who's done it a lot longer and has a lot
more to show me? Um. So, like I'm making this
analogy up on the fly, but like if I were
building a home. Right, if I bought a plot of
land and I want to build a home from scratch,

(28:10):
and I had two people, two contractors come to me
or two architects come to me and show me the
exact same thing. As far as like, here's what we're
gonna do and here's the plan. I'm gonna lean and
probably take the person with twenty more years experience because
I'm being on the fact that they've seen every mistake
can avoid and it can avoid it, and probably have
relationships with you know, the local town government to get

(28:31):
me my permits and things like that. Yeada, YadA, YadA.
But if the person with twenty less years of experience says, hey,
with this plot of land, like, I think you can
go this approach and you can you can dig here,
and you should have extra this here, Like they really
impressed me with creative thinking and innovation and things that
I've been done before. Um, that's when I think you
have to reevaluate. And so with this with the addingency.

(28:53):
You know, yes, I was twenty five, but I think
I was able to earn the respect of the people
that worked for me and the clients that we were
servicing because of the the innovation because what we really
focused on social media back then. Right now, Vader X,
my brother is still the CEO, two thousand employees globally,
super Bowl commercials, everything you would ever expect of an

(29:16):
ad agency. But when we started, we took a very
narrow niche of saying, hey, we think Twitter, Facebook and
social media in general is can be really important. We
think customer attention is going to go that way, and
we think budget is going to go that way. It
sounds really obvious today, but back in two thousand and nine,
we really were. We were looked at as like, these
guys are crazy if they really think that um, And

(29:37):
so that's why we're able to differentiate and win. Right
We had these amazing relationships in Silicon Valley. We had
great ideas. We were coming up with campaigns that were
first and unique and different. We were winning awards and
our clients were getting promoted and it was working. And
so I think eventually it went from that too, you know,
just the experience, Like I don't believe even experienced being

(30:01):
counted in the number of years. I believe in experience
counted in the actual output and product. And so the
point that I made is by the time I was
by the time I was twenty seven, five years in,
I believe I had more experience than nineties something percent
of the market with thirty years experience because we had,
you know, just comparable. If you take the chief operating

(30:24):
officer of an add agency that's been around for thirty
years and they have ten clients and twenty five employees,
they're only going to have so much output in a
given year, Whereas I mean we we had a year
when I was twenty four. We went from employees that
meant I interviewed and hired and onboarded and all these clients,

(30:45):
and so I just think it has to be counted
in terms of experience. Same thing with the sports eating side,
right like, same thing, um, And it was the easy
knock for our competitors, right, oh, don't go with them.
They haven't done X, Y and Z. You don't want
to risk it if you're gonna be a high round
draft pick, etcetera, etcetera. And now I think that's same
things would be really hard for our competition to speak

(31:06):
to because you know, vainer sports me, my my partners,
and my ages. On the football side, for example, we
had two top ten picks. We had Aiden Hunderson go
number two, We Hadawan To go number six. We then
had the second draft a quarterback and Desmond ritter Um.
We had boy A MafA go early second round, and
we also had David Bell go thro around. We had

(31:26):
five top one picks. We just did you know, We
just did Kirk Cousins extension, Ryan Jensen's contracts stay in Tampa,
Allen Robinson to the Rams, Foyer Luacoon second highest a
p y ever for a linebacker, and free agency DJ
reid Um And so you can't you just can't say
the same thing anymore. Right, We've got fifty guys in

(31:47):
the NFL. We we have a lot of success in baseball,
mixed martial arts as well, and so the same things
that our competitors were knocking down two to three years ago, um,
they can't say it anymore. And it's less about, you know,
me being a sports agent for six years. It's more about, like,
I don't want this to come off the wrong way,
but I've accomplished more in the last six months than

(32:09):
some agents doing their entire career. Between the draft and
free agency and some of the other things that we've done.
It don't come off the wrong way through right, Like
it's just black and white true like that. So that's
why I say, like, don't look at me as a
thirty five year old sports agent without a law degree.
Look at me as based on what I've actually done

(32:30):
in the last fifteen years. Right and lindsay, I think
that they, um, you know, you guys look more attractive
to the kids coming out now because I was an
NFL player right rep for eight years and one of
the things we've kept on harping on was changing the
contracts from three percent to one point five percent of
an agent fee. Um, we finally was able to get

(32:52):
that through with the agent has to now negotiate to
the player, Hey, I'm worth the three percent. A lot
of players didn't even know that it was a three
percent max, meaning that the agent could play pay less.
I had no idea. So that's why I ended up
representing myself my last year. But I say that because
players now understand or our understanding slotted money, especially drafted

(33:15):
a slot of money. What I need is somebody to
help me build a brand an image like all that
I need. I need somebody to pound on the table
to bring me money so now they're not looking at
the traditional agent. Hey, it's three percent to enter into
the NFL. We understand that we are already paying three
person what is it three I don't know if it's

(33:35):
changed it since I've been there, but it was three
point one percent of a rookie contract. Uh, salary is
what we pay for NFL P a union. So it's
like I'm already paying three percent for a union that
looks at my contract, I'm gonna pay. You gotta bring
a lot to the table. So I think you guys
are are gonna win and keep on winning, keep going on. No,

(33:58):
I appreciate that, yet to your point, you know the
certain athletes that are out there with the sentiment of,
you know, agents shouldn't get that percent, that full percent.
And what I always say to that is I actually
agree with them to the most for the most part.
But there's exceptions to that rule, and I like to
think that we're one of those exceptions. Right. I think

(34:18):
a very high percentage of agents probably aren't earning their
three Um, there's definitely a group that do. And I
think the other thing too, that I think it's important
for for athletes to keep in mind, you know while
I get on the soapbox to defend the three percent
that we earned, is yeah, I think, like, so we're
I'll use your contract that I'm looking at that came

(34:38):
in at the end. Right, you signed a UH with
the Giants. You signed a four and fourteen, Right, so
you got fourteen some of that guaranteed, some of me not.
But let's assume you know all of that contract gets guaranteed.
You know, fourteen million without the agent fee, right, whereas
fourteen point five million, I've gotta go a little higher.

(35:03):
So fourteen point eight million while paying an agent three percent,
actually nets you out ahead on that fourteen million. I
don't think you representing yourself on that one, but I'm
just speaking like if you had representing yourself on that one.
And so just whenever I run into I've had a
few potential clients highlight, hey, think about doing it myself,
saying saving the percentage or I want you to do

(35:25):
it for one percent and three set of three percent.
Once I start saying hey, like once and I agree
with you. The rookie contract a little bit different. But
when you get to free agency, like I feel really
confident that most capable agents can go and and earn
that three percent just on the difference in either the
guaranteed structure, the legal language, or even the total compensation.

(35:47):
And so um, you know, I think I think it's
an interesting argument to your point. I think a good
chunk don't earn it, but I like to think that
we're in that small group that does. It's awesome. Just so,
just so to to to talk about that, the agent
that I did release from his services gave me a
PenPoint number that I could earn. When I released him,

(36:09):
I got three more millions on my own and so
it's you know, and I saw, so you think about
that three percent I would have had to pay. So
I took that three percent I would have paid him
and created my own company and and then that was
a tax right off, and then I started it. So
I'm like, man, done this a long time ago. But

(36:30):
I think I personally and I do tell players agent
has this place. Um. And I think a lot of
players should lean on their agent more than they actually do. Um.
They're there, they work for you. So UM, a lot
of players don't take a to to you know, not
everybody is as um. I'll just say sharp as you are, right,

(36:52):
not everybody can go and do that themselves. Um. Maybe
they just don't have the aspiration to spend the time
to understand the market and what they're worth, or don't
want to do the negotiation, YadA, YadA, YadA. So I
have had one or two players that have talked to
me about the idea of representing themselves, and I said, listen,
if you're gonna do that, let me prepare you for that, right,

(37:13):
so you do when you do go into free So
I take a lot of pride in like the amount
of time and effort spent with um, the clients that
I'm the lead agent for heading into free agency, just
educating them saying, hey, you know, here are your stats.
Here's your heightweight, speed, here's your medical history. Here's some
comparisons so that you can look so similar to what

(37:33):
your agent did. Um. You know, here's the high end,
here's the low end. UM. And then I keep them
in the loop saying like, hey, here's here's some of
the conversations that I had along the way, and here's
how it went. And you know, I think, um, it's
it's pretty fun. I actually had a client one time, UM,
who thought they wanted to negotiate their own deal. Then

(37:54):
they went through the free agent process, and then we
got the deal done. At the end of it, he goes, bro,
I'm not gonna lie to you. It was just too stressful,
like you're doing my next contract to I just don't
like it. Just stressed, like what you described to me
and how that went down. Like I'm good. I don't
need that in my life now. It's not for everybody, man,

(38:14):
but I do. I have just a few more questions.
I really respect your time and appreciate it. I UM.
When I went to a rookie symposium UM not too
long ago in Vegas, I was asked to come speak
on the panel to talk to some of the younger
guys about how to set yourself up after football. For me,
in any chance to win, Dance with the Stars, right,

(38:36):
and the boat that became a New York Time bestseller,
a lot of things. And I was a seven round
draft pick. Wasn't a guy that was wearing a gold jacket.
I knew I wasn't gonna wear a gold jacket. I
knew it was your average football player, which is still outstanding. UM,
But how do I maximize shot Jennis? That's my thing,
and this guy was on the panel, and every single

(38:57):
reference that he used was pretty much the man. He
used Richard Sherman to explain how wan why he could
do what you do. Um, he used Tom Brady to
explain why he could do what he could do. And
it's like anybody can represent Lebron James or the world.
I mean, when I started representing myself, I was answering call,
saying no more than yes. And so I would love

(39:21):
to allow you to speak to how do you structure
and strategize for your average guy to prepare them for success?
Because there are more NFL talks about the top one
hundred players, but they're sixteen hundred at least annually the play.
So what about the other fifteen hundred? How do you

(39:41):
really represented? No? I love that to your point, like
having a young athlete look at Brady or Sherman doesn't
really teach them a whole lot because step one has
become a Hall of Famer, right, It's like, well, okay,
And then to your point, if you become a Hall
of Famer, it'll fall into place. So I don't think
you can learn a whole lot from that. It's good
to have and I actually, I'll take it back. The

(40:02):
one thing I really love about using those people and
then you've got like Lebron and Kadie and Steph, etcetera,
is that I think there are a tremendous influence on
the next generation. Right, And so you mentioned like I
do believe that athletes are getting smarter and smarter, and
I think the biggest reason is because social media allows
for the distribution of these things that these great athletes

(40:23):
are doing. And so it's great that Lebron and Sherman
and Brady are like making getting on a cap table
and starting a business cool, because previous generations had different
examples what was cool, and it doesn't just bring as
much value as hey like being smart with your money
and meeting the right people and doing business is cool.

(40:44):
Like that's a great thing to teach younger men and women.
So that's awesome. But to answer your question, so number
one thing that I hear um from retired athletes that
I get connected to that they regret is they wigh
did until they were done with the sport to focus
on what they're gonna do when they were done. So

(41:05):
I think the first thing is just always keeping mind.
I tell all my clients that the NFL stands for
not for long. It's my favorite acronym in that regard
because you know it, it's not predictable. There's so many
aspects that control, Like I'm never gonna take away from
an athlete because ultimately, if if a professional athlete ends

(41:25):
up being extremely successful, so much of that is of
their own doing their work, ethic, their natural ability, etcetera. Um,
But I've seen a lot of really talented athletes fail
because of external factors outside of our control. Really two
things predominantly, One UM, injuries, especially in the NFL. Injuries
have really sidelined a lot of people's success. And then two, UM,

(41:49):
it's a real thing. Not to make excuses, but situation.
You get drafted into the wrong environment, you're played out
of position, your positional coach doesn't see your value or
your talent. Like there's a lot of things that jeopardize careers.
And you know, you look at the average length is
in that like two to three year range, and so
you know, you go on and you said it right,
you're an average NFL player, which means you're one of
the most lead athletes in the world. And then you're

(42:11):
out of a job by age and now what and
so the number one thing I always tell all my
guys is UM network and take advantage while you're in
that city. And what I mean by that is like,
no matter what team you play for, Jets, Giants, Cowboys, Niners, Ravens, Dolphins, whatever,

(42:32):
there are people men and women that love that franchise
locally that are very important in the world into what
you may have an interest in, and they care about
you while you're actively wearing the uniform and actively making
a contribution on Sundays. And then the second you're not
wearing that uniform and you're not contributing on Sunday, you

(42:52):
fall into a group of tens of thousands. There's a
lot of former Dolphins, there's a lot of former Cowboys,
and again I'm not taking away from them, but your
your ability to network and make long staying relationships that
can impact you after you're done playing is optimized while
you're playing UM. So that's a big focus. The the
other thing that I think is cool, just to give

(43:13):
anybody listening some examples of not a Hall of Famer
for example, is UM we represent and I represent a
client named Juan Johnson, Juwan um is a tight end
for the New Orleans Saints. Joan's had a very interesting career. Um.
I first got to know Hi when he was at
Penn State as a receiver. He then transferred and did

(43:34):
a grad year at Oregon. He then was receiver at Oregon,
went into the NFL, went undrafted, caught on with the
Saints as a receiver. After his first year, uh, they
converted him too tight end. He was a big receiver,
so he's actually a tight end. Last year he had
four touchdowns last year, which is nice, and his first
year as a tight end. And now he's going into
year three, his second year as a tight end. You know,

(43:56):
he's up the two d fifty pounds, he's starting to
fill out his frame. And the reason I set that
up is, you know, Juwan is somebody that has been cut,
wasn't drafted, has been an active plenty, you know, up
and down between injuries and play play book plans for
that week's opponent. But the one thing that Juan did
do that I think he will be able to utilize

(44:19):
for his entire career no matter what when he's done playing,
is he really latched on to a meeting that we
had internally, we invited all of our clients about two
years ago and change, so I guess maybe seven months
ago during the off season before his second year. Um,
maybe even before his rookie I can't remember the exact timing.

(44:40):
Might have been before his rookie year actually, and Um,
we told everybody in that zoom we had like thirtysothing
people athletes that we were presented in some staff that
for anybody that wants to build a brand and wants
to build an audience, the best platform and the timing
for it was TikTok. He said, TikTok is important. It's
going to explode, and it was already big, but we

(45:00):
said it's going to explode, and thankfully it did. And
so Juan was one of the few athletes. I think
out of the thirty athletes that listened, five created an
account and then out of the five, two or three
of them did it for about three or four weeks
and then quit when they didn't get critical mass. Maybe
they got like a thousand followers off of it. Um,

(45:21):
but then two kept going and so Juwan was one,
and then another one is Isaac Rochelle Um. He's a
defensive end for the Browns now at the time, he
was a charger, seventh round pick out of Notre Dame
and defensive linement, not the most marketable position and uh
boat Juwan and Isaac have amassed a seven figure following

(45:42):
on TikTok and make real money from endorsements off TikTok. Ironically,
they both did something similar where it's a little bit
more on the comedic slant and they both do some
interplay with their SIMI significant other UM. So they're both
married Juan he and his wife Channon have a joint
account and then Isaac and his wife have separate accounts,

(46:03):
but they do a ton of content together and they
both have over a million followers. So you know, two
examples of athletes UM that have had NFL success, but uh,
you know are not I've never been to a Pro Bowl,
are not currently on a B line towards the Hall
of Fame UM, but have focused and put energy off
the field to something that is tangible and it is

(46:24):
a real asset for them moving forward. They have brand,
they have an audience, they have UM hundreds of thousands
of people that care about them and so they could
be contact creators. They could parlay that into different types
of business relationships. Um. I think it's just a good
example of leveraging their and their platform got a boost
because they got to say they were professional football player.
That made them a big unique on TikTok two years ago. Um.

(46:46):
So I think that's a good example to your point,
I love that man, And you're so sound, right. I
can tell you you are articulate your sound. Uh. And
one of the things I think you probably have, um
that you could give credit to yourself as major or awareness.
You know, um, where where you are, where you're from,
who you are, what you represent, how you represent it,
how you sound, and you know it can be very taxing,

(47:09):
a lot of times of thinking heavily so much, and
a lot of responsibility, wearing so many different hats you know,
as a father, as as a as a as a husband,
as a business owner, so many things of pulling at you.
You ought to be successful at it and then your
own DNA, how do you come back to your center,
your muse, your peace, your ground as a business owner, um,

(47:33):
as a father, as all these things. Because a lot
of people you know that are hyper hyperly successful, you
need to find some some type of peace, And I'm
curious is how do you do it? Yeah? No, I
love that question. Um, it's something that what I'll start
with is just try. Like so you mentioned awareness, Um,

(47:55):
something I think that I failed at when I had
less responsibility in my twenties was having that awareness of
listening to my body, what do I need right now? Right?
So I think for anybody that's juggling a lot or
handling a lot, I think self awareness is key and
and giving yourself permission to listen to your body and

(48:17):
find a path towards being in a better spot. Um.
I'm somebody that's a huge believer in mental health. Um.
I look at it, and I'll use a sports analogy
because I always do. There's really two sides to mental health.
I think there's the offense and the defense. So the
defense is therapy. Um, and I'm somebody that benefited tremendously
from therapy in my middle late twenties. Um, I was

(48:40):
at a real low point in my life, primarily around
my physical health. So I suffer from something called Crown's disease.
And my Crown's disease it's um, it's a digestive disease
creates just basically pain and discomfort in your stomach UM
Micron's disease. I had issues and complications with it on
five separate occasions over a twelve month period in which

(49:03):
I had to go to the emergency room. So I
had five trips to the e er uh due to
physical pain in my body. And what happened for me
was UM, those trips to the e er really took
away from like time I had to to get work done,
and then I would stress myself out that I was

(49:23):
behind on work. And the number one thing that actually
triggers crowns is stressed. So it's just this nasty cycle.
If I was getting sick, it was making me behind
on work. I was getting stressed because I was behind
at work, and then I would get sick again, and
so I sought out help and therapy really helped me
work through. And I went to therapy for like two
years UM and I leaned on it heavily once a week,
and it really helped me get there. And then on

(49:45):
the other side is on the offense in terms of
just mental performance and trying like what I describe it as,
I'm trying to take things from good to great with
that and So I've been really consistently working with a
mental performance coach, and and I'm not in a place
where there's any like I'm not in a dark period
of my life. There's Honestly, I'm very happy right now.

(50:06):
But it's that question of like, all right, things are good,
but I don't want to settle for good, Like what
can be better? What can I be like in a
place where things are going well, how can I tinker
and and find things to get better? And so for
me to find that piece one, Um, I've really have
gravitated towards meditation. I'm not perfect with it, and I

(50:27):
don't think I think that's one of the downfalls and
the tricks is that you think you need to be
meditating every single day, five days a year and you
can't miss one. Like I don't do it every day.
I do it a lot though, Um, I do it
during certain times. Sometimes it's not always right when I
wake up. It might be it's recognizing when I'm feeling
stressed and things like that. So meditation and working with
a mental performance coach has been really good. Um. And

(50:50):
then the other thing is I believe everybody has a
place or an activity that can bring you that zen.
So for me, I've only been able to accomplish like
true um detachment from what's going on in my life. Um,
one on a basketball court and then two on a
golf course. Um. So as I get older, I'm thirty

(51:11):
five now, Um, golf has really become like for me
to get out and have a seven a m t
time and it's quiet, I'm outside. Um. I've gotten pretty
good at golf, so that makes it more fun when
you get decent um. But that that's definitely like for me,
and I don't get that year round unfortunately living in
New York, so in that spring summer and I've really

(51:33):
only got like maybe another month left here before I
lose it. Um. You know, getting out there at least
once once a week is my goal for that, and
that's a that's a zen place for me. I love
that you addressed the mental health in regards to your
Crown's disease, because as someone who got diagnosed a few
years ago with an automian disease, the very first thing

(51:54):
that was the most help of them for me was therapy.
And people would think, well, why don't you address the
physicals of them's first, and there's a place for that,
but people don't realize that the mental health aspect is
so important when it comes to work life balance and
to keep your identity and something other than your health.

(52:16):
And so I really related to your answer on that.
So I recently invest or not recently, but a few
years ago, invested in a sub subscribe, subscription based nail
chain called gloss Lab that's all over New York City.
And we have several investors of Maristademeyer, Jared Goff who
are big name athletes. And I realized just how entrepreneurial

(52:42):
athletes are getting and how they want to get into
angel investing because of more money in their contracts and
more guaranteed money. And I guess I mean you are
the king of angel investing. So do these athletes that
you work with come to you to get your advice
on this? And how do you weed out the the

(53:04):
good businesses from the bad? And how many times have
you been wrong? So as far as angel investing, I've
been wrong plenty. I'll start on the last part of
your question. Um, the way I look at it is
like if you look at baseball, if you can go
three for ten every time, you're you're a Hall of Famer, right,
batting three hundreds of incredible mark and you're one of
the best players in the game. And so with angel investing,

(53:25):
especially the earlier stage, I I shoot to be right
one out of ten times, so that means I'm wrong
nine out of ten. But if you're right, and you're
right enough and you're early enough, the r o I
of that investment can outpace all your wrongs. Like unfortunate
enough to say that my investment in Uber covered every
single wrong investment I made when they went I p

(53:46):
O to date right, and so it's like it's a
hits based business. Um. As far as the athletes that
I work with, you know, I'm not a registered financial advisor,
so I need to be careful. I'm not qualified to
give financial advice. But in terms of having high level
casual conversations around business ideas and opportunities, UM, yeah, I

(54:07):
have those conversations all the time. What I do to
make sure that I protect the athlete and protect myself
as I wrope in their financial advisor. UM, and I'm
really passionate about main sure that guys like understand the
downfalls and understand that Yeah, you can be right one
out of ten times and be successful. But just because

(54:27):
you make ten investments doesn't mean any of them are
gonna be right. You could easily go for ten and
so um, I'm just really protective of make sure guys
know that it's an extremely risky asset class um. They
should have a lot of money put away before they
start to partake. Like I'll have you know, late round
draft picks or early career m m A fighters or

(54:49):
minor league baseball players saying they want to do it.
I'm like, hey, like you need to go get the
bag first before you start playing. Like there's a reason
why you hear about Lebron and Katie and Steph and
Richard and Tom. It's because and if you look at
when they started to do this type of activity, Tom
wasn't doing it when he was the Ford string quarterback
in New England's rookie year. He did it once he

(55:10):
you know, was successful. And so I think that's the
other caveats, Just giving guys perspective on like what the
risks are, um, and also making sure that they understand
like where they need to be financially from a security perspective,
and making sure their financial advisor is roped into that
conversation and helping them keep an even head. I love that.
Thank you so much for your time today. This was
so insightful. This was really fun. I appreciate the both

(55:32):
of you. Thank you so much. Absolutely, we'll see on
the sticks, all right, yes, sir, Thanks to you. Thank
you for listening to Sports Illustrated and iHeart Radio Is
the Bag with Rashan Jennings and Lindsay McCormick. For more
podcasts from I heart Radio, visit the I heart Radio app,
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