September 15, 2025 • 39 mins
Jennifer Baron shares her 18-year journey working alongside her principal, Justin, starting as a temp cleaning a file room and eventually becoming Chief of Staff for a private equity firm. She talks about helping manage company growth, supporting multiple portfolio companies, and even working on a historic castle restoration in Scotland. Jennifer also offers practical advice for building a trusted Chief of Staff-principal relationship and setting healthy boundaries.
Links Mentioned:
Free Resources:
- Strategic Planning Checklist
- Chief of Staff Skills Assessment Checklist
- A Day in the Life of a Chief of Staff
- Chief of Staff Toolkit
Get in Touch With Emily:
- Connect on LinkedIn
- Follow on YouTube
- Learn more about coaching
- Sign up for the newsletter
- Clarity Call with Emily
Who Am I?
If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
Time Stamps:
00:31 Discovering Family History
01:54 Jennifer's Career Beginnings
03:43 Meeting Justin and Early Career at Endeavor
05:23 Becoming Chief of Staff
10:03 Private Equity and Company Growth
16:30 Current Role and Responsibilities
19:08 Role of a Chief of Staff in PE Firms
20:43 Building Trust and Dependability
24:44 Evolving Together Over 18 Years
27:41 Adventures in Scotland: A Team-Building Experience
30:55 Advice for Aspiring Chiefs of Staff
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Emily (00:25):
My guest today is Jennifer Baron.
Jennifer, how are you doing?
I'm great.
How are you Emily?
I'm doing all right.
Thanks.
I saw your recent LinkedIn postabout your grandma and you found
like old photos and she was a,what was it, a punch card
operator?
Speaker 2 (00:39):
Yes, like back in the sixties.
Isn't that incredible?
Doing her admin thing?
Yeah.
That's amazing.
Yeah.
I love those pictures.
Um,
Emily (00:48):
yeah.
Speaker 2 (00:48):
Right.
And I have this connection withher that I didn't even know
about until like two weeks ago,so That's amazing.
Was that just out of a
Emily (00:55):
box from like someone's house of
Speaker 2 (00:57):
photos?
Yeah.
Yeah, my grandfather's house.
And we just went througheverything and we found all
kinds of amazing things.
So that was very exciting.
Emily (01:05):
I love that.
I love doing that.
Where you find a whole box ofphotos.
'cause it's not on a computer,it's actual physical photos.
Yes.
And it's like these photos tella story, which Yes.
You get to uncover.
So that was super cool.
And it's so funny'cause I sawthe post and I thought it was.
Like, you can see the familyresemblance a little bit.
I'm like, oh, yep, that's yourgrandma.
Got it.
Yes, yes.
(01:27):
Um, fantastic.
But thank you so much forjoining.
You have a really interestingchief of staff story.
Uh, I think you win for thelongest partnership with your
principal, which is 18 years.
Is it 18?
That's correct.
Wow.
I'm
Speaker 2 (01:41):
surprised.
Like I didn't realize I was.
Such, such a, an anomaly that'slike with this tenure,
Emily (01:48):
a full adult person who can vote.
That's, that's a long time.
That's a lot of hairstyles, Jen.
Um, yes, but I wanna hear aboutlike your origin story, how you
met Justin, how you got to bechief of staff, and, um, all of
those good things.
So kick us off from the verybeginning.
Speaker 2 (02:05):
Yeah, so I'd love to kind of go through the
highlights of our journeytogether.
Um, starting with, my storyactually starts with failure,
um, which is how I ended upmeeting Justin in the first
place.
So, uh, I started as anadministrative assistant in the
mortgage industry right out ofcollege, and I worked my way up
to Loan closer, and theneventually manager of the
(02:28):
closing department.
But what I didn't know was thatI was not ready to manage
people.
Um, so I was, ended up being aperfect case study for someone
who's really good at their joband gets promoted, but then
fails due to lack of leadershiptraining.
Um, so January, 2007, thefinancial crisis hits and I get
laid off because of downsizing.
(02:50):
So I'm back to square one, justa few years straight outta
college.
Um.
So the things that I learnedfrom that experience was I
didn't wanna be in an industryas volatile and unstable as
mortgages.
So I kind of took that off thetable completely.
Um, and then I also realizedthat I was not ready to manage
(03:10):
people, at least not at thatpoint in my career.
Um, so because of the financialcrisis, job prospects at the
time were not great.
So I figured that my best optionwould be to sign up with a temp
agency.
I had done that during highschool and it worked out really
well for me.
I had steady work, so I figuredwhy not, you know, I was also
looking for jobs, but that waskind of a stop gap.
(03:32):
Um, so I got a call from thetemp agency and they had an
assignment in Alpharetta, whichis a suburb, suburb of Atlanta,
but it's about 40 minutes fromwhere we lived.
So I was thinking, you know, Ireally do need something to do,
but I'm not willing to commutethat far if this turns into
something more lucrative.
(03:54):
So I declined that and the nextday got a call for a job about
15 minutes from our house.
So I took that and this is thepart of the story that I look
back on and I wonder, dideverything.
Did the universe already haveeverything laid out for me?
So I show up at my assignmentand it's for an administrative
(04:15):
temp position at EndeavorTelecom.
Uh, in February of 2007 andJustin is the CEO of this
company.
So that's how we first met.
I'm a temp in his office and myfirst assignment is cleaning up
this file room that was just incomplete shambles.
Um, so.
Organizing things is literallyone of my favorite things to do.
(04:36):
So I was like, yes, this isperfect.
Um, you know, I got that taskdone quickly.
Who doesn't love a greatorganization challenge, right?
Um, so then they startedassigning me other projects and
within a couple months I agreedto stay on as a permanent
administrative assistant.
Um, so I was supporting multipleexecutives, project management,
(04:59):
sales, and the accountingdepartment, and I started to
work more closely with Justin.
So that is kind of the beginningof our story, starting as a temp
and then agreeing to stay on asan admin with
Emily (05:11):
his company.
That last part you said is likeinching toward chief of staff
land.
I can sense it, I can feel it.
Speaker 2 (05:18):
Okay.
Not yet, but almost gimme acouple years.
So, uh, that was February of2007.
By December of 2007, um, wedecided that.
Because I was working on morekind of executive projects, a
title change was, was warranted.
(05:39):
So my title became, uh, managerof Executive Initiatives.
So I was driving projects thatwere, um, things that Justin and
his business partner wanted topush through, but they were
working on strategic stuff.
So they just need somebody tokind of keep an eye on things
and make sure things are stayingmoving with these projects.
(05:59):
And with that, I started tobecome the voice of the CEO
within the company.
Um, so Justin started to trustme and he was willing to let me
be his representative, which wasreally cool.
Um, and around that same time,we had a big conversation where
we basically agreed to kind ofmerge our careers together, um,
(06:22):
and keep working with each otheras long as it was a positive
partnership.
So.
I was like, wow, this isincredible.
Emily (06:30):
Yeah.
Wait, tell me more about that.
You just like decided one daywe're just gonna stick together
for a long time, just dependingon our different roles.
Speaker 2 (06:39):
Whoa.
Yeah.
Emily (06:40):
Yeah.
Speaker 2 (06:40):
It's
Emily (06:40):
really
Speaker 2 (06:41):
crazy to think back on now.
Emily (06:43):
What?
What made you guys do that?
Speaker 2 (06:45):
We work together so well.
We compliment each other.
He's the risk taker.
I keep us grounded, you know,he's the dreamer and I'm the
doer.
Um, so it was just, it worked.
You know what I mean?
Yeah.
And the thing that I was mostappreciative of was that he kind
of, he accepted me for who Iwas, um, which means.
(07:09):
He valued my own nonsenseapproach.
Um, he appreciated the fact thatI was super focused on getting
things done because I think itwas exactly what he needed at
the time.
Um, and that I was anintelligent person, so I didn't
have to hide who I really was tosucceed with him, if that makes
(07:29):
sense.
So that made me feel verycomfortable.
Um.
And you know, the, the storythere is when you're allowed to
be yourself, you're, you have abetter chance of success instead
of worrying about, you know whatI mean?
Like worrying about whatsituation you're in and how do
you need to change in order tofit when you can be yourself.
(07:50):
It's just easy and you can focuson getting things done and
handling stuff that you need todo.
Emily (07:55):
I love that.
I love that when you're fullyyourself and it.
That makes it even morecomplimentary to the other
person.
Like that's a good spot to be inwhere it's like, okay, I just
need to like lean into what I amjust already doing, my
strengths, what I'm about.
And that fits so perfectlywithin this case, Justin's
strength.
'cause he can be fully who heis.
(08:16):
Go off and vision and dream andtake risks.
And that's just, that's, I lovethat.
Okay.
So that's kind of, so it'spretty incredible.
Felt that, and were like, let'sjust do this thing together for
a while.
Yes.
Okay.
Okay.
Because
Speaker 2 (08:28):
when he, when he started Endeavor, he always
knew, one of the things he lovesto say is start with the end in
mind.
So when he started this company,he knew that eventually he would
sell it.
So he knew that there werebigger things that he wanted to
do, and he wanted to kind ofbring me along for all that
stuff.
So.
Gotcha.
Okay.
It's pretty awesome.
Emily (08:49):
Now, are you officially chief of staff yet, or not yet?
No, not yet.
That's coming.
Okay.
But you're doing a lot of chiefof staff stuff.
It's like you're the voice ofthe CEO, you're doing the
strategic projects.
Okay.
Exactly.
Speaker 2 (09:01):
Yep.
So as a company, endeavor wasgrowing.
When I first started there, wehad about 30 employees.
Uh, within a few years we had130 employees.
So.
The need for the manager ofexecutive initiatives position
and eventually chief of staffresulted from this company
growth.
Um, I interface between middlemanagement and the executives,
(09:24):
and I always listen forimportant information that I
felt that I should share withthem because I.
People felt comfortable with me.
I was building relationships andthey told me things that they
probably wouldn't go to Justin'soffice and tell him.
Um, so I was adding value therebecause I was hearing things
that they wouldn't hear in thenormal course of business.
(09:45):
Um, and I also advocated for themanagers and the staff, uh, to
support initiatives that wouldimprove operations.
So if they came to me and said,Hey, we're having a really tough
time with this new thing thatwe've implemented, you know, I'd
bring that feedback to theexecutives and.
Help to make something betterfor everybody.
Nice.
So, so now a couple years later,2009, we start to talk to a
(10:09):
private equity firm out ofMiami, and eventually that led
to a recapitalization in Marchof 2010.
So, I mean, you know about duediligence, Emily, it's a big
part of private equity.
Oh yes.
So they're doing their duediligence on, on Endeavor.
Um, Justin's in all thesemeetings, he is got all these
data requests, so I'm helpinghim scheduling the meetings and
(10:33):
fulfilling all these requeststhat we've got.
So everything checks out, youknow, the recap goes through
March of 2010.
And even though I'd only beenwith the company for about three
years at that point, I was therefor that large growth phase.
So I had a ton of institutionalknowledge and I was able to help
the whole process, you know,with all these things that I
(10:54):
knew.
Um, so two really cool thingsabout the recap.
Um, one of the things that thisprivate equity firm likes to do
is when they do a transaction,they offer employees a chance to
buy into some equity in thecompany.
And I had never done anythinglike that before, but a, a good
(11:14):
number of the management teambought in and that was kind of
my first taste of investing.
We'd never done anything likethat.
It was very exciting.
Um, and then the second part ofthat is that Justin, when they
were, you know, writing all thedocuments, all the legal
documents, he made sure therewas a clause in there that he
(11:35):
could bring me with him.
Whenever he left the company.
Okay.
So he could bring one employeeand that was me.
Wow.
So that just kind of, but youknow, when we had that deal to
work together, this was kind ofthe next step of that.
Whatever he goes to do next, I'mgonna go with him.
Got it.
In writing
Emily (11:55):
in a clause.
Way to go.
Justin, there's your, there's aprinciple for you.
Alright.
Yes.
Okay.
Speaker 2 (12:02):
Um, okay.
So let's fast forward a little,a few months.
We're into the summer of 2010and we've gone through this big
recap.
We're growing the company.
And I'm continuing to functionas ju as Justin's right person,
right hand person.
Um, and then I have aconversation with one of my
friends that summer that kind ofchanges the trajectory of my
(12:22):
career.
So he's telling me about his newposition at SunTrust Bank.
Um, he was the chief of stafffor the Enterprise Services,
enterprise Delivery Servicesgroup at the bank.
And he's telling me about allthese responsibilities that he
has and I'm like, wait a second.
That's all the stuff I'm alreadydoing.
So the wheels are turning in myhead.
(12:43):
I'm like, what can I do withthis?
So I end up generating aproposal to bring to Justin and
say, Hey, what do you thinkabout me assuming the title of
chief of staff?
These are all the things thatchiefs of staff do.
I'm already doing like 85% ofthem.
So he was immediately like, yes,this sounds great.
(13:04):
I love it.
Especially because with therecap.
My role became external facingas well.
So I'm talking to people outsideof the company and Justin wanted
to make sure that we wereconveying my position as his
right hand person.
And when you've got a title likemanager of Executive initiatives
(13:25):
that we literally made up, whenI took that title, everybody's
like, we don't know what thatis, who are you?
But when you hear chief ofStaff, you're like, oh.
I see what's going on.
Nice.
So that, that was accomplishinga, a goal, a goal for me to
accelerate my career, but alsoto represent the company with
(13:48):
what I was actually doing and myrole.
So it was a win-win.
Very cool.
Emily (13:53):
Yeah.
And which is pretty
Speaker 2 (13:54):
exciting.
Emily (13:55):
Yeah.
And just like one call out, likethat's really important when
even internally when you needto, you have a large company and
you wanna convey like.
What you do.
Mm-hmm.
Having the title and, and beingable to, my principal used to
say like, I need you to be ableto bring the thunder if you need
to.
And I was like, got it.
So, yes.
Um, but externally too, peoplecan, can, it helps them place
(14:15):
it.
So I'm glad he did that for you.
I'm glad you advocated for itand he did that for you, but
gotcha.
Yes.
Cool.
So now you're officially chiefof staff.
Speaker 2 (14:23):
Yes.
Uh, September of 2010, Ibelieve, is when all that
happened.
Okay.
Um, so let's fast forward to2012.
Like I mentioned, Justin alwaysknew that he was eventually
going to exit the company.
So we hire a gentleman whostarts off as COO and then
eventually assumes that the CEOrole within the company.
(14:44):
So at that point, Justin becomesthe executive chairman and I'm
supporting him still as chief ofstaff.
Um, to, you know, keep an eye onthings, make sure that the new
CEO has everything that he needsto be successful.
Um, and we were able to startthinking about kind of what's
next.
(15:05):
So we, he wanted to open aprivate equity firm and family
office, so I was like, yes, I'mon board.
Let's do it.
Um, and when we eventually do,you know.
We're doing private equity fulltime.
We talked about changing mytitle because at that point it
wasn't a large company anymore.
(15:26):
It was a very small office.
Um, but he was like, no, we'regonna keep it because it, we
still need to convey what yourposition is.
So I appreciated that.
I would've been fine withwhatever, but.
He said, let's keep it, youknow, this is great.
We'll just move forward withthis.
Um, so fast forward a couplemore years.
Endeavor merges with a companycalled OnePath and it formed a
(15:50):
company of several thousandemployees.
So at that point we would gofrom 30 to like 150 to like
several thousand, which was mindblowing.
Um, the Endeavor management teamstayed on as the management team
for the new company.
And Justin continued asexecutive chairman, me as his
chief of staff.
(16:10):
Um, and then in October of 17,we sold one Path so that we
could focus on Dewar Mallbusiness full time.
Um, and we had a lucrative exitfrom that equity that we had
purchased back in 2010.
Hey, so that was very exciting.
Yes.
So that leads us to today.
Um, it's kind of been businessas usual since then with me as
(16:35):
Justin's chief of staff anddoing private equity and family
office matters.
Emily (16:40):
Wow.
Okay.
So you're at DUR Mall now?
Yes.
Mm-hmm.
Yes.
Okay.
So today you said business asusual, like itself.
If we did some PE exits, we grewthe company, thousands of
people, dah, dah, dah, dah.
Um, what is your scope ofresponsibility and work now, and
how do you balance?
It seems like Justin is in awhole bunch of different areas
and doing a whole bunch ofdifferent things.
Speaker 2 (17:01):
Yeah.
Um, so my, right now our firm isinvolved in direct investments
and co-investments, and we aresupporting our direct
investments, which we call ourportfolio companies on a daily
basis.
So that means that I'm stayingconnected with those management
teams, keeping an eye on what'sgoing on.
(17:21):
Am I hearing anything thatJustin needs to know about, kind
of like what I did in Endeavor,right?
Um, and.
I am also supporting the dotmall business, which is general,
you know, regular businessstuff, um, and supporting Justin
on his personal matters so thathe can focus on strategy and
(17:42):
planning and big picture stufffor the portfolio companies.
Emily (17:46):
So, hold on, just to make sure I'm tracking.
You have like PE firm thatJustin has with the Port cos?
Yes.
And so you're working with likethe leadership teams at each of
those portfolio companies andkind of being the, the catalyst
or conduit between Justin andthose management teams?
Yes.
That's a huge job in and ofitself, but you're doing that.
and then what about the.
(18:08):
Like the dot mall, is thatseparate or is that like the
umbrella piece, or is that aseparate?
That's kind of the
Speaker 2 (18:12):
umbrella.
Emily (18:13):
Okay.
Yeah.
And then you have, so everything
Speaker 2 (18:15):
falls under that,
Emily (18:16):
and then you have the whole personal stuff, which I
don't want to get into hispersonal stuff, but you're like
chief of staffing, all of thatarena as well?
Yes.
Okay.
How do you do that?
How do you balance
Speaker 2 (18:29):
that?
Yeah.
Um, so I'm really good withboundaries, so I use the time
blocking method.
To focus on one thing for a setamount of time, usually a Port
Co.
And then the next thing I'mmoving to is the next Port Co.
So I'm not like shifting backand forth every five minutes.
I'm kind of focusing my time onthat, on one thing, handling all
(18:52):
that, moving to the next thing,handling all that.
And then it's kinda like thiscycle that goes over the course
of the day.
Right.
Um, and.
Where was I going with that?
I don't even know.
No
Emily (19:06):
worries.
I'm just curious too.
Like I, I've seen, um, PE firmshave a chief of staff at like
the firm level, and then I'vehad them have a chief of staff
as an operating partner thatthey deploy into their port
codes.
To like actually be in theoperations of that business.
Um, so I'm wondering, it soundslike you're more, um, like the
liaison or conduit between thetwo.
(19:28):
Are you ever involved in like,okay, because I know about this
part of the operations, I know apart about this functional area,
I can actually like be a littlebit more hands-on.
Are you kind of, uh, more highlevel than that?
Speaker 2 (19:39):
We do get hands on, um, because.
As you know, when entrepreneursstart a company, they don't
think about certain things likeHR and taxes and finance and
those things.
They're more focused on theirbig idea and how to get it off
the ground and how to make a tonof money right now.
Um, so that's kind of where wecome in.
We, our value added services arethings like accounting and taxes
(20:01):
and things like that.
Gotcha.
And HR and things that theseguys don't think about.
So, gotcha.
Very cool.
Yeah, so I'm not, I'm not likeworking for the companies, but I
like in the companies, but I amdoing things for them on a
regular basis.
Gotcha.
Emily (20:18):
Okay.
Yeah, that makes sense.
I mean, one of the advantages ofPE firms is they bring those
resources and networks andpartners and hey, like, we can
help you out by standing upthis, you know, fractional HR
piece or whatnot, and just.
Get things stood up so they cango.
Exactly.
Speaker 2 (20:33):
Okay.
Yep.
And then eventually thecompanies get big enough to hire
their own people and do thatsort of thing, but we kind of
fill the gap.
Gotcha.
So that they can get things.
On board.
Very cool.
Emily (20:43):
Very cool.
Yeah.
So you've been in this like longtrajectory with Justin and I'm
wondering, you know, 18 years,like I said, is a long time.
Mm-hmm.
And just as like growth as aperson, you must have changed in
those 18 years and Justin, I'massuming changed and, and has
grown as a person.
So how did you evolve?
Like what's the.
Dynamic like between you two andwhat was that, um, like at the
(21:05):
beginning and now it's how it isnow.
How did that evolve, uh,together?
Speaker 2 (21:09):
Yeah.
Um, so obviously some thingshave stayed the same, but a lot
has changed'cause we're verydifferent people now than we
were, you know, 18 years ago.
Um, so Justin has been my mentorbasically from the start, which
is really cool.
Um, he.
(21:32):
Obviously when we startedworking together, I didn't have
a whole lot of professionalexperience.
I'd had one job outta collegeand I didn't know a lot, but I
didn't know what I didn't know.
So he suggested topics for myprofessional development, like
finance, investment, projectmanagement, uh, marketing, and
even like telecom basics becausewe at Endeavor at that time.
(21:53):
Um, and he, he is a very smartperson.
Um, he's probably the smartestperson I know and by the time we
started working together, he hadalready started multiple
businesses and worked ininternational sales.
So he is got a ton of experienceand I can learn from him and I
was happy to do that.
Um.
And you know, just thinking backto like that first day in the
(22:16):
file room, one of the thingsabout me is that I take a lot of
pride in my work.
So yes, I've been a manager amonth before that, but now I'm
starting this next phase in mycareer and I totally don't mind
getting in these file cabinetsand figuring out where
everything needs to go.
Like, I'm not afraid to roll upmy sleeves and do whatever needs
to be done.
(22:38):
And I take pride in my work.
So Justin realized that he coulddepend on me pretty quickly
because he is given me thesethings to do and I'm getting
them done.
I'm getting them done quicklyand accurately.
So that started to build thetrust of our relationship,
right?
Um, if I tell you I'm gonna dosomething, I'm gonna do it.
If I tell you I'm gonna besomewhere at a certain time,
I'll be there.
(22:59):
Don't worry about it.
Um, in fact, I had a colleagueat one point in my career who
told me that he could set hiswatch by my schedule because I
was always like showing up atthe office at 7 45, going to
lunch at 12 o'clock.
You know, so that to me bigcompliment because I want people
to be able to depend on me.
Nice.
Um.
(23:19):
So as the trust grew in ourrelationship, our partnerships
evolving, I became increasinglyinvolved in his family and
personal business, um, and thecommunity and the philanthropic
endeavors that he was workingon.
And it might sound a littleweird that.
I would be so mired in somebodyelse's life that is not my
(23:42):
spouse or not a member of myfamily.
Um, but we had been veryintentional to work on our
relationship and making surethat Justin and my husband knew
each other and knew each otherwell, and that I knew his
family.
And, you know, it kind of goteverything ingrained together so
(24:02):
that.
Everybody was comfortable withthe situation, if that makes
sense.
Emily (24:06):
Totally.
Yeah.
I think, I mean, that's a reallygood point.
'cause you're spending loads oftime with this person.
It is, uh, I mean, I was gonnasay intense relationship.
It is a very, like, you're veryclose and you're doing a lot of
things together, and you'respending a lot of time and
you're sharing a lot ofinformation, especially on the
personal side.
So I think, uh, I, I like thatyou said.
We were intentional aboutworking on our relationship and
(24:28):
then intentional about, youknow, making sure that he knew
my husband very well.
So everyone is, is.
Is good with the differentdynamics that are happening.
Speaker 2 (24:38):
Yes, yes.
So I'm glad that we worked onthat because it made things
easier as time went on.
Gotcha.
Essentially.
Um, so when we started workingtogether, we were both under 30
years old, which if you thinkback to yourself that young, you
were completely different personthan you are now.
Um, so we.
We grew together professionallyover the years.
(25:00):
We are both so much more patientand empathetic and
understanding, and it creates avery positive work environment,
which I appreciate.
Um, and we've also supportedeach other kind of through
professional and personal upsand downs through our lives.
Like we've 18 years, a lot ofstuff happens and I'm glad that
(25:20):
we have each other to kind oflean on when things aren't
great, but also to celebratewhen things are really great.
That's awesome.
Um, so that's really cool.
Um, so for me, I have gotten alot more comfortable with
initiating uncomfortableconversations.
Um.
By default, I hateconfrontation.
(25:41):
So for me to decide to work onthat and get a lot better at it
was a huge thing.
Um, you know, we're in this forthe long haul, so let's make the
effort to provide real timefeedback and continue building
our trust and improve ourrelationship.
So that was a big investmentthat I made, you know, to, to
(26:02):
improve our relationship andbuild the trust.
Emily (26:05):
Are you willing to say like what kind of things you did
to work on that?
It sounds like it was like anintentional, I need to get, I
wanna get better at this for thelong-term success.
Let me put some steps in place.
Was that just, was that just,okay, I'm gonna put myself
outside my comfort zone?
Or were there other stepsinvolved in that?
Speaker 2 (26:21):
Putting myself way outside my comfort zone.
Um, if I observe something in ameeting, you know, I, I would
kind of file it away.
But then at, at some point I waslike, you know what, this isn't
doing me any good, keeping allthese things in my brain, so I
need to start sharing thisstuff.
And even though, like I knewthat he wasn't going to get mad
(26:41):
about anything that I said, butit was still like, oh my God,
I'm so uncomfortable.
I don't know if I can do this.
So I, you know, I, the pointwhere I.
I want this to be successful, soI need to go outside my comfort
zone and work on these thingswith him.
So,
Emily (26:56):
and it sounds like, yeah, that was a huge thing.
It sounds like the response waspretty positive, or at least it
got to a positive point in theend.
Speaker 2 (27:03):
Yes, absolutely.
Yep.
Which is very good.
Um, and then just to kind ofillustrate our partnership.
I would say that Justin is oneof the people I would call if my
house was burning down in themiddle of the night.
Like I, I think that speaksvolumes to kind of where we are
and how much we trust each otherand how strong our relationship
(27:25):
is, so, wow.
Wow.
That's, yeah, I think that'spretty incredible.
Emily (27:29):
From the file file room to calling, you know, emergency
contact, the house is literallyburning down.
Justin, please help me.
Speaker 2 (27:38):
Yes, yes.
Well, hey, let's actually goback.
I wanted to talk a little bitabout Justin's kind of
extracurricular activities thatI involved.
A number of nonprofit andphilanthropic endeavors, and
this includes a foundation boardat a university and an
(27:59):
international historicrestoration project, um, which
is to restore do castle on theIsle of Mall in Scotland.
Um, the castle has been aroundsince 1360, so it's a pretty
important part of history.
So, I mean, I have been involvedwith nonprofits for all of my
professional life.
So when he decided to getinvolved in this, I was like,
(28:21):
yes, this is amazing.
Let's do this.
Um, so in 2017, we actually wentto Scotland to see the castle,
and we were able to meet SirLocklin, who is the kind of the
head of the McLean clan.
Um, so we were invited to thecastle for dinner while we were
there, so we get to the.
(28:42):
To the door.
And Sir Lachlan's son answersthe door and he says, oh my
gosh, we just lost power in thedining room.
We're gonna have to have dinnerby candlelight.
Oh.
And we were like, what?
So that was amazing.
Um, I guess when you have areally old castle, things like
that just randomly happened,right?
I wouldn't know, but I amassuming yes.
(29:03):
Yes, I think it does.
So we have the dinner.
We had venison that washarvested from the castle
grounds, which is incredible.
Um, I'm from Pennsylvania.
My family hunts, so that'ssomething that I'm a hundred
percent on board with.
So we finish dinner, we gooutside.
It's like 10 o'clock at nightand the sun is just starting to
set because mall is like reallyfar north.
(29:27):
This was in June, so it'ssummertime, but we look out over
the water because the castlekind of sits on the edge of the
island.
It's on the, on the coast, andwe look out over the water and
the sky is like this purple andorange color.
And it was incredible.
Um, I, I was like, wow, I justhad candlelight dinner at a
castle and now I'm seeing thisamazing sunset.
(29:49):
Like all these cool things arehappening.
Um.
So on that trip we also took ahelicopter ride, which is my
first time in a helicopter.
Um, and then we hiked to the topof Ben Moore, which is the
tallest point on the Isle ofMole.
And it ended up being a reallygood team building exercise
because you're looking at BenMoore from the C level and
(30:11):
you're like, oh, that doesn'tlook too bad.
It'll take a couple hours, butthen you start to get to the top
and it gets harder and harder.
Um, but we made it and we wereso proud of each other that we
were able to do that.
Um, so after the fact.
I call Scotland my bucket listtrip that I didn't even know I
wanted to do because we did somany cool things.
(30:31):
So,
Emily (30:32):
wow, that's an amazing story.
That tells me, um, I need to upmy game on team building
exercises that they can involvea castle.
Uh, yeah.
So Jen, you not only win for 18year tenure with your principal,
you win for the, uh.
Only Castle Initiative thatwe've had on the show.
Love.
So that is, that is amazing.
(30:53):
Um, beautiful.
To round us out here, let's justdo lightning round.
What advice would you give tochiefs of staff who are, you
know, looking to get into therole for the first time, or
existing chiefs of staff?
And then I'll ask you same thingfor principals, but just, uh,
yes, I've got some thoughts onthis.
Yeah.
Speaker 2 (31:10):
Um, let's see.
So if you're a new chief ofstaff or you think you wanna
become one, um.
I think the, the main foundationis the relationship.
If you wanna be successful,you've gotta have that
relationship with yourprincipal.
Um, you know, we made a bigeffort to build it over the
(31:32):
years, we're still working onit, and at the end of the day,
relationships are the secretsauce for a team.
Whether you've got two people,20 people, or 200 people.
Um, we had a lot ofsimilarities.
You know, we're close in age,similar Gen X experiences
growing up.
Um, and like I said earlier,neither of us are afraid to roll
(31:52):
up our sleeves if there'ssomething that needs to be done.
Um, we're not afraid to do thehard work.
Um, so take the time to findcommon ground and build that
relationship and you'll becomeindispensable, um, because
you'll become the person thatyour principal trusts, and
that's huge.
So you've got, you're working onyour foundation, you're starting
to build trust, get comfortablewith the uncomfortable stuff.
(32:15):
Um, I feel like one of my rolesis being Justin's truth teller.
I'm gonna tell'em things thatother people might not say.
Um, a lot of executives don'treceive candid feedback and
they're kind of, you know, in abubble almost.
And chiefs of staff can becomethat person to.
(32:38):
Say the things that nobody elseis going to tell them.
Um, and when you, like I said,having the uncomfortable
conversations.
It's important, but approach itfrom a, from a place of helping
instead of confronting.
So start out a conversationlike, Hey, you know, in the
(32:58):
meeting yesterday, I noticedsomething that happened.
I wanted to chat with you aboutit.
Um, instead of going in gunsblazing, like ready to fight,
because that's not productive atall.
Um, and then I also think it'simportant for chiefs of staff to
be sounding boards.
We almost always know thesecrets that nobody else knows,
(33:19):
but.
You wanna also become thatperson that they come to when
they need advice, when they'renot sure what to do.
Um, so I think one good way todo that is, you know, that your
principal had a board meetingyesterday, follow up and say,
Hey, how did everything goyesterday?
Do we need to do any follow up?
Um, kind of get put yourself inthe position to be the person
(33:42):
that they're gonna come to thenext time for important
conversations like that.
And then don't be afraid to jumpin and offer suggestions because
you might have an experiencefrom your past.
Positions that could apply towhatever you and your principal
are going through at this time.
(34:03):
And a lot of executives sufferfrom decision fatigue, right?
Um, so most of the time they'regonna be willing to give you the
reins on some things.
Um, once you've got that trustbuilt, become the person that
they're going to come to whenthey need something, you know,
handled and.
(34:23):
So, yeah, ingrain yourself.
Um, become the trusted person,become the signing board, become
the truth teller, and make surethat you keep developing that
relationship.
So that's my advice for a newchief of staff.
And then as far as somebodywho's thinking about getting a
chief of staff or might alreadyhave one, if you don't have one
(34:45):
yet.
Ensure that you, you are readyto bring on somebody in that
position.
Um, the best chiefs of staff arethe people who have access to
everything and their principalsare not afraid of delegating.
Um, if you are not a gooddelegator, I think you need to
(35:06):
put that on hold.
Don't hire a chief of staff.
Um, do some.
Reflection and deep diving tofigure out what is it about
delegation that you're afraidof, because you've gotta fix
that before you can bringsomebody on in this important
position.
Um, and I'm gonna quote TylerParis.
He wrote the chief of staff bookin 2015, and he did a ton of
(35:30):
interviews with HR people,executives, and chiefs of staff.
To kind of figure out whatreally makes this role work.
And he said that the executive'sunwillingness to delegate was
the number one reason that therole failed.
So it's super important as aprincipal, you need to delegate.
And if you're not ready to dothat, don't hire a chief of
(35:51):
staff yet.
Um, and then if you are ready,consider the people that you've
already got on your team.
Uh, do you have a strongrelationship and some level of
trust with somebody that youalready know on your team?
Uh, do you see potential in anyof your current team members for
strategic thinking, strategicexecution, things like that?
(36:13):
Um, for me, starting a chief ofseveral relationship with
somebody you already know inanother capacity, kind of
eliminates half of theuncertainty right off the bat.
If you already have a beginningof a relationship and you
already trust'em.
You know, if you think they can,you know, stand up to the
challenge, then they're probablya good person to look at as you
(36:35):
think about hiring a chief ofstaff.
And then the last wisdom on partis that if you have a chief of
staff and you wanna optimizethem, make sure that you're
focusing on keeping buildingthat relationship as time goes
on.
Because relationships are likeplants.
They need certain things tothrive.
(36:58):
And this to me means havingconversations about things that
aren't about work, right?
So in, I have a story aboutthis.
In the summer of 2022, we'restarting to emerge from Covid.
You know, everybody's completelystressed out and tired of
everything.
But I was kind of reflecting andI thought to myself.
(37:21):
It doesn't feel like Justin andI are driving like we did a few
years ago.
So I was like, Hey, do you, areyou interested in maybe grabbing
a drink once a month?
Just that we have time outsideof the office to talk about
personal things?
He said, yes, that's a greatidea.
So we've been doing that eversince.
It's almost three years now, andit's really good to just have
(37:42):
time where you're not talkingabout the portfolio company.
Yeah.
And you're talking about otherthings, and that's how you build
the relationship.
So keep develop, developing it.
It's kind of, it's kind of likeleadership.
It's a journey.
It's not a destination.
Right.
So it's something you alwayshave to work on.
Emily (38:00):
Yes.
I love that.
'cause it's just a differentkind of conversation, just
different topics, but also liketone and tenor and just setting
and everything.
I think that is so important.
And is it wrong that like.
You said, if you're not readyfor a chief of staff and you're
not ready to give full accessand to delegate, then you might
wanna take a look at that andyou might not be ready for a
chief of staff.
Is it wrong that I wanted tostart clapping at that part?
(38:22):
Like, oh my gosh, like this isamazing.
You absolutely
Speaker 2 (38:24):
should clap at that.
Oh my gosh.
Everyone needs to hear that.
You don't wanna bring somebodyin and then set them up.
For failure?
No, to me that's not fair.
Emily (38:33):
It's a two-way street.
This is a very, you know, yougotta, it's complimentary
dynamic.
You gotta make sure you clickand have rapport, like it's a
two-way street.
You gotta be ready too.
So I love, love, love.
Exactly that.
You mentioned that.
So thank you.
Um, yes, Jen, if anyone wants toreach out to you, wants to know
more about the PE firm, um,where, where's the best place to
find that information?
Speaker 2 (38:54):
Well, we've got our website do mall.com, and I'm on
LinkedIn like all the time, sofeel free to reach out to me on
LinkedIn.
Emily (39:03):
We'll have those links in the show notes.
And just to spell Doer,D-U-A-R-T mall.
MALL?
Yes.
M-U-L-L-M-U-L-L.
Gotcha.
Okay.
We'll have the link in the shownotes.
And Jen, thank you so much.
It's been, um, it's been funhearing your story and it's been
fun hearing about your 18.
Your tenure and partnership withJustin and your really cool
(39:24):
castle initiative.
I am.
I'm not gonna lie.
I'm a little jealous that yougot to have that as one of your
initiatives as Chief of staff.
So thank you so much for sharingyour story.
Appreciate it.
Thank you.
My guest today is Jennifer Baron.
Jennifer, how are you doing?
I'm great.
How are you Emily?
I'm doing all right.
Thanks.
I saw your recent LinkedIn postabout your grandma and you found
like old photos and she was a,what was it, a punch card
operator?
Speaker 2 (00:39):
Yes, like back in the sixties.
Isn't that incredible?
Doing her admin thing?
Yeah.
That's amazing.
Yeah.
I love those pictures.
Um,
Emily (00:48):
yeah.
Speaker 2 (00:48):
Right.
And I have this connection withher that I didn't even know
about until like two weeks ago,so That's amazing.
Was that just out of a
Emily (00:55):
box from like someone's house of
Speaker 2 (00:57):
photos?
Yeah.
Yeah, my grandfather's house.
And we just went througheverything and we found all
kinds of amazing things.
So that was very exciting.
Emily (01:05):
I love that.
I love doing that.
Where you find a whole box ofphotos.
'cause it's not on a computer,it's actual physical photos.
Yes.
And it's like these photos tella story, which Yes.
You get to uncover.
So that was super cool.
And it's so funny'cause I sawthe post and I thought it was.
Like, you can see the familyresemblance a little bit.
I'm like, oh, yep, that's yourgrandma.
Got it.
Yes, yes.
(01:27):
Um, fantastic.
But thank you so much forjoining.
You have a really interestingchief of staff story.
Uh, I think you win for thelongest partnership with your
principal, which is 18 years.
Is it 18?
That's correct.
Wow.
I'm
Speaker 2 (01:41):
surprised.
Like I didn't realize I was.
Such, such a, an anomaly that'slike with this tenure,
Emily (01:48):
a full adult person who can vote.
That's, that's a long time.
That's a lot of hairstyles, Jen.
Um, yes, but I wanna hear aboutlike your origin story, how you
met Justin, how you got to bechief of staff, and, um, all of
those good things.
So kick us off from the verybeginning.
Speaker 2 (02:05):
Yeah, so I'd love to kind of go through the
highlights of our journeytogether.
Um, starting with, my storyactually starts with failure,
um, which is how I ended upmeeting Justin in the first
place.
So, uh, I started as anadministrative assistant in the
mortgage industry right out ofcollege, and I worked my way up
to Loan closer, and theneventually manager of the
(02:28):
closing department.
But what I didn't know was thatI was not ready to manage
people.
Um, so I was, ended up being aperfect case study for someone
who's really good at their joband gets promoted, but then
fails due to lack of leadershiptraining.
Um, so January, 2007, thefinancial crisis hits and I get
laid off because of downsizing.
(02:50):
So I'm back to square one, justa few years straight outta
college.
Um.
So the things that I learnedfrom that experience was I
didn't wanna be in an industryas volatile and unstable as
mortgages.
So I kind of took that off thetable completely.
Um, and then I also realizedthat I was not ready to manage
(03:10):
people, at least not at thatpoint in my career.
Um, so because of the financialcrisis, job prospects at the
time were not great.
So I figured that my best optionwould be to sign up with a temp
agency.
I had done that during highschool and it worked out really
well for me.
I had steady work, so I figuredwhy not, you know, I was also
looking for jobs, but that waskind of a stop gap.
(03:32):
Um, so I got a call from thetemp agency and they had an
assignment in Alpharetta, whichis a suburb, suburb of Atlanta,
but it's about 40 minutes fromwhere we lived.
So I was thinking, you know, Ireally do need something to do,
but I'm not willing to commutethat far if this turns into
something more lucrative.
(03:54):
So I declined that and the nextday got a call for a job about
15 minutes from our house.
So I took that and this is thepart of the story that I look
back on and I wonder, dideverything.
Did the universe already haveeverything laid out for me?
So I show up at my assignmentand it's for an administrative
(04:15):
temp position at EndeavorTelecom.
Uh, in February of 2007 andJustin is the CEO of this
company.
So that's how we first met.
I'm a temp in his office and myfirst assignment is cleaning up
this file room that was just incomplete shambles.
Um, so.
Organizing things is literallyone of my favorite things to do.
(04:36):
So I was like, yes, this isperfect.
Um, you know, I got that taskdone quickly.
Who doesn't love a greatorganization challenge, right?
Um, so then they startedassigning me other projects and
within a couple months I agreedto stay on as a permanent
administrative assistant.
Um, so I was supporting multipleexecutives, project management,
(04:59):
sales, and the accountingdepartment, and I started to
work more closely with Justin.
So that is kind of the beginningof our story, starting as a temp
and then agreeing to stay on asan admin with
Emily (05:11):
his company.
That last part you said is likeinching toward chief of staff
land.
I can sense it, I can feel it.
Speaker 2 (05:18):
Okay.
Not yet, but almost gimme acouple years.
So, uh, that was February of2007.
By December of 2007, um, wedecided that.
Because I was working on morekind of executive projects, a
title change was, was warranted.
(05:39):
So my title became, uh, managerof Executive Initiatives.
So I was driving projects thatwere, um, things that Justin and
his business partner wanted topush through, but they were
working on strategic stuff.
So they just need somebody tokind of keep an eye on things
and make sure things are stayingmoving with these projects.
(05:59):
And with that, I started tobecome the voice of the CEO
within the company.
Um, so Justin started to trustme and he was willing to let me
be his representative, which wasreally cool.
Um, and around that same time,we had a big conversation where
we basically agreed to kind ofmerge our careers together, um,
(06:22):
and keep working with each otheras long as it was a positive
partnership.
So.
I was like, wow, this isincredible.
Emily (06:30):
Yeah.
Wait, tell me more about that.
You just like decided one daywe're just gonna stick together
for a long time, just dependingon our different roles.
Speaker 2 (06:39):
Whoa.
Yeah.
Emily (06:40):
Yeah.
Speaker 2 (06:40):
It's
Emily (06:40):
really
Speaker 2 (06:41):
crazy to think back on now.
Emily (06:43):
What?
What made you guys do that?
Speaker 2 (06:45):
We work together so well.
We compliment each other.
He's the risk taker.
I keep us grounded, you know,he's the dreamer and I'm the
doer.
Um, so it was just, it worked.
You know what I mean?
Yeah.
And the thing that I was mostappreciative of was that he kind
of, he accepted me for who Iwas, um, which means.
(07:09):
He valued my own nonsenseapproach.
Um, he appreciated the fact thatI was super focused on getting
things done because I think itwas exactly what he needed at
the time.
Um, and that I was anintelligent person, so I didn't
have to hide who I really was tosucceed with him, if that makes
(07:29):
sense.
So that made me feel verycomfortable.
Um.
And you know, the, the storythere is when you're allowed to
be yourself, you're, you have abetter chance of success instead
of worrying about, you know whatI mean?
Like worrying about whatsituation you're in and how do
you need to change in order tofit when you can be yourself.
(07:50):
It's just easy and you can focuson getting things done and
handling stuff that you need todo.
Emily (07:55):
I love that.
I love that when you're fullyyourself and it.
That makes it even morecomplimentary to the other
person.
Like that's a good spot to be inwhere it's like, okay, I just
need to like lean into what I amjust already doing, my
strengths, what I'm about.
And that fits so perfectlywithin this case, Justin's
strength.
'cause he can be fully who heis.
(08:16):
Go off and vision and dream andtake risks.
And that's just, that's, I lovethat.
Okay.
So that's kind of, so it'spretty incredible.
Felt that, and were like, let'sjust do this thing together for
a while.
Yes.
Okay.
Okay.
Because
Speaker 2 (08:28):
when he, when he started Endeavor, he always
knew, one of the things he lovesto say is start with the end in
mind.
So when he started this company,he knew that eventually he would
sell it.
So he knew that there werebigger things that he wanted to
do, and he wanted to kind ofbring me along for all that
stuff.
So.
Gotcha.
Okay.
It's pretty awesome.
Emily (08:49):
Now, are you officially chief of staff yet, or not yet?
No, not yet.
That's coming.
Okay.
But you're doing a lot of chiefof staff stuff.
It's like you're the voice ofthe CEO, you're doing the
strategic projects.
Okay.
Exactly.
Speaker 2 (09:01):
Yep.
So as a company, endeavor wasgrowing.
When I first started there, wehad about 30 employees.
Uh, within a few years we had130 employees.
So.
The need for the manager ofexecutive initiatives position
and eventually chief of staffresulted from this company
growth.
Um, I interface between middlemanagement and the executives,
(09:24):
and I always listen forimportant information that I
felt that I should share withthem because I.
People felt comfortable with me.
I was building relationships andthey told me things that they
probably wouldn't go to Justin'soffice and tell him.
Um, so I was adding value therebecause I was hearing things
that they wouldn't hear in thenormal course of business.
(09:45):
Um, and I also advocated for themanagers and the staff, uh, to
support initiatives that wouldimprove operations.
So if they came to me and said,Hey, we're having a really tough
time with this new thing thatwe've implemented, you know, I'd
bring that feedback to theexecutives and.
Help to make something betterfor everybody.
Nice.
So, so now a couple years later,2009, we start to talk to a
(10:09):
private equity firm out ofMiami, and eventually that led
to a recapitalization in Marchof 2010.
So, I mean, you know about duediligence, Emily, it's a big
part of private equity.
Oh yes.
So they're doing their duediligence on, on Endeavor.
Um, Justin's in all thesemeetings, he is got all these
data requests, so I'm helpinghim scheduling the meetings and
(10:33):
fulfilling all these requeststhat we've got.
So everything checks out, youknow, the recap goes through
March of 2010.
And even though I'd only beenwith the company for about three
years at that point, I was therefor that large growth phase.
So I had a ton of institutionalknowledge and I was able to help
the whole process, you know,with all these things that I
(10:54):
knew.
Um, so two really cool thingsabout the recap.
Um, one of the things that thisprivate equity firm likes to do
is when they do a transaction,they offer employees a chance to
buy into some equity in thecompany.
And I had never done anythinglike that before, but a, a good
(11:14):
number of the management teambought in and that was kind of
my first taste of investing.
We'd never done anything likethat.
It was very exciting.
Um, and then the second part ofthat is that Justin, when they
were, you know, writing all thedocuments, all the legal
documents, he made sure therewas a clause in there that he
(11:35):
could bring me with him.
Whenever he left the company.
Okay.
So he could bring one employeeand that was me.
Wow.
So that just kind of, but youknow, when we had that deal to
work together, this was kind ofthe next step of that.
Whatever he goes to do next, I'mgonna go with him.
Got it.
In writing
Emily (11:55):
in a clause.
Way to go.
Justin, there's your, there's aprinciple for you.
Alright.
Yes.
Okay.
Speaker 2 (12:02):
Um, okay.
So let's fast forward a little,a few months.
We're into the summer of 2010and we've gone through this big
recap.
We're growing the company.
And I'm continuing to functionas ju as Justin's right person,
right hand person.
Um, and then I have aconversation with one of my
friends that summer that kind ofchanges the trajectory of my
(12:22):
career.
So he's telling me about his newposition at SunTrust Bank.
Um, he was the chief of stafffor the Enterprise Services,
enterprise Delivery Servicesgroup at the bank.
And he's telling me about allthese responsibilities that he
has and I'm like, wait a second.
That's all the stuff I'm alreadydoing.
So the wheels are turning in myhead.
(12:43):
I'm like, what can I do withthis?
So I end up generating aproposal to bring to Justin and
say, Hey, what do you thinkabout me assuming the title of
chief of staff?
These are all the things thatchiefs of staff do.
I'm already doing like 85% ofthem.
So he was immediately like, yes,this sounds great.
(13:04):
I love it.
Especially because with therecap.
My role became external facingas well.
So I'm talking to people outsideof the company and Justin wanted
to make sure that we wereconveying my position as his
right hand person.
And when you've got a title likemanager of Executive initiatives
(13:25):
that we literally made up, whenI took that title, everybody's
like, we don't know what thatis, who are you?
But when you hear chief ofStaff, you're like, oh.
I see what's going on.
Nice.
So that, that was accomplishinga, a goal, a goal for me to
accelerate my career, but alsoto represent the company with
(13:48):
what I was actually doing and myrole.
So it was a win-win.
Very cool.
Emily (13:53):
Yeah.
And which is pretty
Speaker 2 (13:54):
exciting.
Emily (13:55):
Yeah.
And just like one call out, likethat's really important when
even internally when you needto, you have a large company and
you wanna convey like.
What you do.
Mm-hmm.
Having the title and, and beingable to, my principal used to
say like, I need you to be ableto bring the thunder if you need
to.
And I was like, got it.
So, yes.
Um, but externally too, peoplecan, can, it helps them place
(14:15):
it.
So I'm glad he did that for you.
I'm glad you advocated for itand he did that for you, but
gotcha.
Yes.
Cool.
So now you're officially chiefof staff.
Speaker 2 (14:23):
Yes.
Uh, September of 2010, Ibelieve, is when all that
happened.
Okay.
Um, so let's fast forward to2012.
Like I mentioned, Justin alwaysknew that he was eventually
going to exit the company.
So we hire a gentleman whostarts off as COO and then
eventually assumes that the CEOrole within the company.
(14:44):
So at that point, Justin becomesthe executive chairman and I'm
supporting him still as chief ofstaff.
Um, to, you know, keep an eye onthings, make sure that the new
CEO has everything that he needsto be successful.
Um, and we were able to startthinking about kind of what's
next.
(15:05):
So we, he wanted to open aprivate equity firm and family
office, so I was like, yes, I'mon board.
Let's do it.
Um, and when we eventually do,you know.
We're doing private equity fulltime.
We talked about changing mytitle because at that point it
wasn't a large company anymore.
(15:26):
It was a very small office.
Um, but he was like, no, we'regonna keep it because it, we
still need to convey what yourposition is.
So I appreciated that.
I would've been fine withwhatever, but.
He said, let's keep it, youknow, this is great.
We'll just move forward withthis.
Um, so fast forward a couplemore years.
Endeavor merges with a companycalled OnePath and it formed a
(15:50):
company of several thousandemployees.
So at that point we would gofrom 30 to like 150 to like
several thousand, which was mindblowing.
Um, the Endeavor management teamstayed on as the management team
for the new company.
And Justin continued asexecutive chairman, me as his
chief of staff.
(16:10):
Um, and then in October of 17,we sold one Path so that we
could focus on Dewar Mallbusiness full time.
Um, and we had a lucrative exitfrom that equity that we had
purchased back in 2010.
Hey, so that was very exciting.
Yes.
So that leads us to today.
Um, it's kind of been businessas usual since then with me as
(16:35):
Justin's chief of staff anddoing private equity and family
office matters.
Emily (16:40):
Wow.
Okay.
So you're at DUR Mall now?
Yes.
Mm-hmm.
Yes.
Okay.
So today you said business asusual, like itself.
If we did some PE exits, we grewthe company, thousands of
people, dah, dah, dah, dah.
Um, what is your scope ofresponsibility and work now, and
how do you balance?
It seems like Justin is in awhole bunch of different areas
and doing a whole bunch ofdifferent things.
Speaker 2 (17:01):
Yeah.
Um, so my, right now our firm isinvolved in direct investments
and co-investments, and we aresupporting our direct
investments, which we call ourportfolio companies on a daily
basis.
So that means that I'm stayingconnected with those management
teams, keeping an eye on what'sgoing on.
(17:21):
Am I hearing anything thatJustin needs to know about, kind
of like what I did in Endeavor,right?
Um, and.
I am also supporting the dotmall business, which is general,
you know, regular businessstuff, um, and supporting Justin
on his personal matters so thathe can focus on strategy and
(17:42):
planning and big picture stufffor the portfolio companies.
Emily (17:46):
So, hold on, just to make sure I'm tracking.
You have like PE firm thatJustin has with the Port cos?
Yes.
And so you're working with likethe leadership teams at each of
those portfolio companies andkind of being the, the catalyst
or conduit between Justin andthose management teams?
Yes.
That's a huge job in and ofitself, but you're doing that.
and then what about the.
(18:08):
Like the dot mall, is thatseparate or is that like the
umbrella piece, or is that aseparate?
That's kind of the
Speaker 2 (18:12):
umbrella.
Emily (18:13):
Okay.
Yeah.
And then you have, so everything
Speaker 2 (18:15):
falls under that,
Emily (18:16):
and then you have the whole personal stuff, which I
don't want to get into hispersonal stuff, but you're like
chief of staffing, all of thatarena as well?
Yes.
Okay.
How do you do that?
How do you balance
Speaker 2 (18:29):
that?
Yeah.
Um, so I'm really good withboundaries, so I use the time
blocking method.
To focus on one thing for a setamount of time, usually a Port
Co.
And then the next thing I'mmoving to is the next Port Co.
So I'm not like shifting backand forth every five minutes.
I'm kind of focusing my time onthat, on one thing, handling all
(18:52):
that, moving to the next thing,handling all that.
And then it's kinda like thiscycle that goes over the course
of the day.
Right.
Um, and.
Where was I going with that?
I don't even know.
No
Emily (19:06):
worries.
I'm just curious too.
Like I, I've seen, um, PE firmshave a chief of staff at like
the firm level, and then I'vehad them have a chief of staff
as an operating partner thatthey deploy into their port
codes.
To like actually be in theoperations of that business.
Um, so I'm wondering, it soundslike you're more, um, like the
liaison or conduit between thetwo.
(19:28):
Are you ever involved in like,okay, because I know about this
part of the operations, I know apart about this functional area,
I can actually like be a littlebit more hands-on.
Are you kind of, uh, more highlevel than that?
Speaker 2 (19:39):
We do get hands on, um, because.
As you know, when entrepreneursstart a company, they don't
think about certain things likeHR and taxes and finance and
those things.
They're more focused on theirbig idea and how to get it off
the ground and how to make a tonof money right now.
Um, so that's kind of where wecome in.
We, our value added services arethings like accounting and taxes
(20:01):
and things like that.
Gotcha.
And HR and things that theseguys don't think about.
So, gotcha.
Very cool.
Yeah, so I'm not, I'm not likeworking for the companies, but I
like in the companies, but I amdoing things for them on a
regular basis.
Gotcha.
Emily (20:18):
Okay.
Yeah, that makes sense.
I mean, one of the advantages ofPE firms is they bring those
resources and networks andpartners and hey, like, we can
help you out by standing upthis, you know, fractional HR
piece or whatnot, and just.
Get things stood up so they cango.
Exactly.
Speaker 2 (20:33):
Okay.
Yep.
And then eventually thecompanies get big enough to hire
their own people and do thatsort of thing, but we kind of
fill the gap.
Gotcha.
So that they can get things.
On board.
Very cool.
Emily (20:43):
Very cool.
Yeah.
So you've been in this like longtrajectory with Justin and I'm
wondering, you know, 18 years,like I said, is a long time.
Mm-hmm.
And just as like growth as aperson, you must have changed in
those 18 years and Justin, I'massuming changed and, and has
grown as a person.
So how did you evolve?
Like what's the.
Dynamic like between you two andwhat was that, um, like at the
(21:05):
beginning and now it's how it isnow.
How did that evolve, uh,together?
Speaker 2 (21:09):
Yeah.
Um, so obviously some thingshave stayed the same, but a lot
has changed'cause we're verydifferent people now than we
were, you know, 18 years ago.
Um, so Justin has been my mentorbasically from the start, which
is really cool.
Um, he.
(21:32):
Obviously when we startedworking together, I didn't have
a whole lot of professionalexperience.
I'd had one job outta collegeand I didn't know a lot, but I
didn't know what I didn't know.
So he suggested topics for myprofessional development, like
finance, investment, projectmanagement, uh, marketing, and
even like telecom basics becausewe at Endeavor at that time.
(21:53):
Um, and he, he is a very smartperson.
Um, he's probably the smartestperson I know and by the time we
started working together, he hadalready started multiple
businesses and worked ininternational sales.
So he is got a ton of experienceand I can learn from him and I
was happy to do that.
Um.
And you know, just thinking backto like that first day in the
(22:16):
file room, one of the thingsabout me is that I take a lot of
pride in my work.
So yes, I've been a manager amonth before that, but now I'm
starting this next phase in mycareer and I totally don't mind
getting in these file cabinetsand figuring out where
everything needs to go.
Like, I'm not afraid to roll upmy sleeves and do whatever needs
to be done.
(22:38):
And I take pride in my work.
So Justin realized that he coulddepend on me pretty quickly
because he is given me thesethings to do and I'm getting
them done.
I'm getting them done quicklyand accurately.
So that started to build thetrust of our relationship,
right?
Um, if I tell you I'm gonna dosomething, I'm gonna do it.
If I tell you I'm gonna besomewhere at a certain time,
I'll be there.
(22:59):
Don't worry about it.
Um, in fact, I had a colleagueat one point in my career who
told me that he could set hiswatch by my schedule because I
was always like showing up atthe office at 7 45, going to
lunch at 12 o'clock.
You know, so that to me bigcompliment because I want people
to be able to depend on me.
Nice.
Um.
(23:19):
So as the trust grew in ourrelationship, our partnerships
evolving, I became increasinglyinvolved in his family and
personal business, um, and thecommunity and the philanthropic
endeavors that he was workingon.
And it might sound a littleweird that.
I would be so mired in somebodyelse's life that is not my
(23:42):
spouse or not a member of myfamily.
Um, but we had been veryintentional to work on our
relationship and making surethat Justin and my husband knew
each other and knew each otherwell, and that I knew his
family.
And, you know, it kind of goteverything ingrained together so
(24:02):
that.
Everybody was comfortable withthe situation, if that makes
sense.
Emily (24:06):
Totally.
Yeah.
I think, I mean, that's a reallygood point.
'cause you're spending loads oftime with this person.
It is, uh, I mean, I was gonnasay intense relationship.
It is a very, like, you're veryclose and you're doing a lot of
things together, and you'respending a lot of time and
you're sharing a lot ofinformation, especially on the
personal side.
So I think, uh, I, I like thatyou said.
We were intentional aboutworking on our relationship and
(24:28):
then intentional about, youknow, making sure that he knew
my husband very well.
So everyone is, is.
Is good with the differentdynamics that are happening.
Speaker 2 (24:38):
Yes, yes.
So I'm glad that we worked onthat because it made things
easier as time went on.
Gotcha.
Essentially.
Um, so when we started workingtogether, we were both under 30
years old, which if you thinkback to yourself that young, you
were completely different personthan you are now.
Um, so we.
We grew together professionallyover the years.
(25:00):
We are both so much more patientand empathetic and
understanding, and it creates avery positive work environment,
which I appreciate.
Um, and we've also supportedeach other kind of through
professional and personal upsand downs through our lives.
Like we've 18 years, a lot ofstuff happens and I'm glad that
(25:20):
we have each other to kind oflean on when things aren't
great, but also to celebratewhen things are really great.
That's awesome.
Um, so that's really cool.
Um, so for me, I have gotten alot more comfortable with
initiating uncomfortableconversations.
Um.
By default, I hateconfrontation.
(25:41):
So for me to decide to work onthat and get a lot better at it
was a huge thing.
Um, you know, we're in this forthe long haul, so let's make the
effort to provide real timefeedback and continue building
our trust and improve ourrelationship.
So that was a big investmentthat I made, you know, to, to
(26:02):
improve our relationship andbuild the trust.
Emily (26:05):
Are you willing to say like what kind of things you did
to work on that?
It sounds like it was like anintentional, I need to get, I
wanna get better at this for thelong-term success.
Let me put some steps in place.
Was that just, was that just,okay, I'm gonna put myself
outside my comfort zone?
Or were there other stepsinvolved in that?
Speaker 2 (26:21):
Putting myself way outside my comfort zone.
Um, if I observe something in ameeting, you know, I, I would
kind of file it away.
But then at, at some point I waslike, you know what, this isn't
doing me any good, keeping allthese things in my brain, so I
need to start sharing thisstuff.
And even though, like I knewthat he wasn't going to get mad
(26:41):
about anything that I said, butit was still like, oh my God,
I'm so uncomfortable.
I don't know if I can do this.
So I, you know, I, the pointwhere I.
I want this to be successful, soI need to go outside my comfort
zone and work on these thingswith him.
So,
Emily (26:56):
and it sounds like, yeah, that was a huge thing.
It sounds like the response waspretty positive, or at least it
got to a positive point in theend.
Speaker 2 (27:03):
Yes, absolutely.
Yep.
Which is very good.
Um, and then just to kind ofillustrate our partnership.
I would say that Justin is oneof the people I would call if my
house was burning down in themiddle of the night.
Like I, I think that speaksvolumes to kind of where we are
and how much we trust each otherand how strong our relationship
(27:25):
is, so, wow.
Wow.
That's, yeah, I think that'spretty incredible.
Emily (27:29):
From the file file room to calling, you know, emergency
contact, the house is literallyburning down.
Justin, please help me.
Speaker 2 (27:38):
Yes, yes.
Well, hey, let's actually goback.
I wanted to talk a little bitabout Justin's kind of
extracurricular activities thatI involved.
A number of nonprofit andphilanthropic endeavors, and
this includes a foundation boardat a university and an
(27:59):
international historicrestoration project, um, which
is to restore do castle on theIsle of Mall in Scotland.
Um, the castle has been aroundsince 1360, so it's a pretty
important part of history.
So, I mean, I have been involvedwith nonprofits for all of my
professional life.
So when he decided to getinvolved in this, I was like,
(28:21):
yes, this is amazing.
Let's do this.
Um, so in 2017, we actually wentto Scotland to see the castle,
and we were able to meet SirLocklin, who is the kind of the
head of the McLean clan.
Um, so we were invited to thecastle for dinner while we were
there, so we get to the.
(28:42):
To the door.
And Sir Lachlan's son answersthe door and he says, oh my
gosh, we just lost power in thedining room.
We're gonna have to have dinnerby candlelight.
Oh.
And we were like, what?
So that was amazing.
Um, I guess when you have areally old castle, things like
that just randomly happened,right?
I wouldn't know, but I amassuming yes.
(29:03):
Yes, I think it does.
So we have the dinner.
We had venison that washarvested from the castle
grounds, which is incredible.
Um, I'm from Pennsylvania.
My family hunts, so that'ssomething that I'm a hundred
percent on board with.
So we finish dinner, we gooutside.
It's like 10 o'clock at nightand the sun is just starting to
set because mall is like reallyfar north.
(29:27):
This was in June, so it'ssummertime, but we look out over
the water because the castlekind of sits on the edge of the
island.
It's on the, on the coast, andwe look out over the water and
the sky is like this purple andorange color.
And it was incredible.
Um, I, I was like, wow, I justhad candlelight dinner at a
castle and now I'm seeing thisamazing sunset.
(29:49):
Like all these cool things arehappening.
Um.
So on that trip we also took ahelicopter ride, which is my
first time in a helicopter.
Um, and then we hiked to the topof Ben Moore, which is the
tallest point on the Isle ofMole.
And it ended up being a reallygood team building exercise
because you're looking at BenMoore from the C level and
(30:11):
you're like, oh, that doesn'tlook too bad.
It'll take a couple hours, butthen you start to get to the top
and it gets harder and harder.
Um, but we made it and we wereso proud of each other that we
were able to do that.
Um, so after the fact.
I call Scotland my bucket listtrip that I didn't even know I
wanted to do because we did somany cool things.
(30:31):
So,
Emily (30:32):
wow, that's an amazing story.
That tells me, um, I need to upmy game on team building
exercises that they can involvea castle.
Uh, yeah.
So Jen, you not only win for 18year tenure with your principal,
you win for the, uh.
Only Castle Initiative thatwe've had on the show.
Love.
So that is, that is amazing.
(30:53):
Um, beautiful.
To round us out here, let's justdo lightning round.
What advice would you give tochiefs of staff who are, you
know, looking to get into therole for the first time, or
existing chiefs of staff?
And then I'll ask you same thingfor principals, but just, uh,
yes, I've got some thoughts onthis.
Yeah.
Speaker 2 (31:10):
Um, let's see.
So if you're a new chief ofstaff or you think you wanna
become one, um.
I think the, the main foundationis the relationship.
If you wanna be successful,you've gotta have that
relationship with yourprincipal.
Um, you know, we made a bigeffort to build it over the
(31:32):
years, we're still working onit, and at the end of the day,
relationships are the secretsauce for a team.
Whether you've got two people,20 people, or 200 people.
Um, we had a lot ofsimilarities.
You know, we're close in age,similar Gen X experiences
growing up.
Um, and like I said earlier,neither of us are afraid to roll
(31:52):
up our sleeves if there'ssomething that needs to be done.
Um, we're not afraid to do thehard work.
Um, so take the time to findcommon ground and build that
relationship and you'll becomeindispensable, um, because
you'll become the person thatyour principal trusts, and
that's huge.
So you've got, you're working onyour foundation, you're starting
to build trust, get comfortablewith the uncomfortable stuff.
(32:15):
Um, I feel like one of my rolesis being Justin's truth teller.
I'm gonna tell'em things thatother people might not say.
Um, a lot of executives don'treceive candid feedback and
they're kind of, you know, in abubble almost.
And chiefs of staff can becomethat person to.
(32:38):
Say the things that nobody elseis going to tell them.
Um, and when you, like I said,having the uncomfortable
conversations.
It's important, but approach itfrom a, from a place of helping
instead of confronting.
So start out a conversationlike, Hey, you know, in the
(32:58):
meeting yesterday, I noticedsomething that happened.
I wanted to chat with you aboutit.
Um, instead of going in gunsblazing, like ready to fight,
because that's not productive atall.
Um, and then I also think it'simportant for chiefs of staff to
be sounding boards.
We almost always know thesecrets that nobody else knows,
(33:19):
but.
You wanna also become thatperson that they come to when
they need advice, when they'renot sure what to do.
Um, so I think one good way todo that is, you know, that your
principal had a board meetingyesterday, follow up and say,
Hey, how did everything goyesterday?
Do we need to do any follow up?
Um, kind of get put yourself inthe position to be the person
(33:42):
that they're gonna come to thenext time for important
conversations like that.
And then don't be afraid to jumpin and offer suggestions because
you might have an experiencefrom your past.
Positions that could apply towhatever you and your principal
are going through at this time.
(34:03):
And a lot of executives sufferfrom decision fatigue, right?
Um, so most of the time they'regonna be willing to give you the
reins on some things.
Um, once you've got that trustbuilt, become the person that
they're going to come to whenthey need something, you know,
handled and.
(34:23):
So, yeah, ingrain yourself.
Um, become the trusted person,become the signing board, become
the truth teller, and make surethat you keep developing that
relationship.
So that's my advice for a newchief of staff.
And then as far as somebodywho's thinking about getting a
chief of staff or might alreadyhave one, if you don't have one
(34:45):
yet.
Ensure that you, you are readyto bring on somebody in that
position.
Um, the best chiefs of staff arethe people who have access to
everything and their principalsare not afraid of delegating.
Um, if you are not a gooddelegator, I think you need to
(35:06):
put that on hold.
Don't hire a chief of staff.
Um, do some.
Reflection and deep diving tofigure out what is it about
delegation that you're afraidof, because you've gotta fix
that before you can bringsomebody on in this important
position.
Um, and I'm gonna quote TylerParis.
He wrote the chief of staff bookin 2015, and he did a ton of
(35:30):
interviews with HR people,executives, and chiefs of staff.
To kind of figure out whatreally makes this role work.
And he said that the executive'sunwillingness to delegate was
the number one reason that therole failed.
So it's super important as aprincipal, you need to delegate.
And if you're not ready to dothat, don't hire a chief of
(35:51):
staff yet.
Um, and then if you are ready,consider the people that you've
already got on your team.
Uh, do you have a strongrelationship and some level of
trust with somebody that youalready know on your team?
Uh, do you see potential in anyof your current team members for
strategic thinking, strategicexecution, things like that?
(36:13):
Um, for me, starting a chief ofseveral relationship with
somebody you already know inanother capacity, kind of
eliminates half of theuncertainty right off the bat.
If you already have a beginningof a relationship and you
already trust'em.
You know, if you think they can,you know, stand up to the
challenge, then they're probablya good person to look at as you
(36:35):
think about hiring a chief ofstaff.
And then the last wisdom on partis that if you have a chief of
staff and you wanna optimizethem, make sure that you're
focusing on keeping buildingthat relationship as time goes
on.
Because relationships are likeplants.
They need certain things tothrive.
(36:58):
And this to me means havingconversations about things that
aren't about work, right?
So in, I have a story aboutthis.
In the summer of 2022, we'restarting to emerge from Covid.
You know, everybody's completelystressed out and tired of
everything.
But I was kind of reflecting andI thought to myself.
(37:21):
It doesn't feel like Justin andI are driving like we did a few
years ago.
So I was like, Hey, do you, areyou interested in maybe grabbing
a drink once a month?
Just that we have time outsideof the office to talk about
personal things?
He said, yes, that's a greatidea.
So we've been doing that eversince.
It's almost three years now, andit's really good to just have
(37:42):
time where you're not talkingabout the portfolio company.
Yeah.
And you're talking about otherthings, and that's how you build
the relationship.
So keep develop, developing it.
It's kind of, it's kind of likeleadership.
It's a journey.
It's not a destination.
Right.
So it's something you alwayshave to work on.
Emily (38:00):
Yes.
I love that.
'cause it's just a differentkind of conversation, just
different topics, but also liketone and tenor and just setting
and everything.
I think that is so important.
And is it wrong that like.
You said, if you're not readyfor a chief of staff and you're
not ready to give full accessand to delegate, then you might
wanna take a look at that andyou might not be ready for a
chief of staff.
Is it wrong that I wanted tostart clapping at that part?
(38:22):
Like, oh my gosh, like this isamazing.
You absolutely
Speaker 2 (38:24):
should clap at that.
Oh my gosh.
Everyone needs to hear that.
You don't wanna bring somebodyin and then set them up.
For failure?
No, to me that's not fair.
Emily (38:33):
It's a two-way street.
This is a very, you know, yougotta, it's complimentary
dynamic.
You gotta make sure you clickand have rapport, like it's a
two-way street.
You gotta be ready too.
So I love, love, love.
Exactly that.
You mentioned that.
So thank you.
Um, yes, Jen, if anyone wants toreach out to you, wants to know
more about the PE firm, um,where, where's the best place to
find that information?
Speaker 2 (38:54):
Well, we've got our website do mall.com, and I'm on
LinkedIn like all the time, sofeel free to reach out to me on
LinkedIn.
Emily (39:03):
We'll have those links in the show notes.
And just to spell Doer,D-U-A-R-T mall.
MALL?
Yes.
M-U-L-L-M-U-L-L.
Gotcha.
Okay.
We'll have the link in the shownotes.
And Jen, thank you so much.
It's been, um, it's been funhearing your story and it's been
fun hearing about your 18.
Your tenure and partnership withJustin and your really cool
(39:24):
castle initiative.
I am.
I'm not gonna lie.
I'm a little jealous that yougot to have that as one of your
initiatives as Chief of staff.
So thank you so much for sharingyour story.
Appreciate it.
Thank you.
Popular Podcasts
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.