All Episodes

April 24, 2025 28 mins

Craig shares his concerns about the industry's brain trust that will soon retire, and the importance of passing information to future generations.  He also explains the importance of listening in building one’s network and how discretion is integral in doing deals.  Finally, Craig shares the 3 Magic Words that go a long way in a successful career.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Lan Elliott (00:00):
Hello and welcome to its Personal Stories.
My name is Lan Elliot on behalfof its personal stories, and I
am really happy to have a recentfriend, but he's just so much
fun and I am really thrilled tohave Craig Sullivan on our show
today.
Welcome, Craig,

Craig Sullivan (00:19):
man.
Thank you so much.
It's great to be here.
I really appreciate this.
Thank you.

Lan Elliott (00:24):
I have realized that every time I talk to you, I
learn something new about youbecause you have had a really
fascinating career.
Of course, now you are thefounder and head of Click Media.
You have an incredible clickconference that you do.
Each year in California, but youhave had so many different

(00:47):
chapters.
I would love to learn about yourcareer journey and what are
really the pivot points or theinflections in your career, and
if there's something you thinkhas been a factor in your
success along the way.

Craig Sullivan (01:02):
Yeah, great question.
First off, there have been a lotof changes, a lot of diversity,
and.
I attribute it to severalpeople.
My mother being one of them mydad being another, but people
that I worked for and with thatreally helped shape my

(01:24):
impressions and my ability toget things done.
And seeing people that don'tnecessarily care about
associates that said, Nope, Inever wanna be that person.
But it I was basically leavingthe entertainment industry and
my parents said, okay, you'rejust floundering, doing nothing,

(01:46):
coming to work, family business.
So that was real estate, and I,my first exposure was on the
residential.
Absolutely hated it.
It was just the lack of decorumand.
Professionalism, peoplescreaming to get things done.
And I understand that's anemotional buy for, okay, it's a

(02:09):
lot of money.
Typically their largestinvestment, so on and and I got
into subdivisions and newconstruction of tracks and then
eventually made it over tocommercial and discovered
hospitality.
And I went, oh boy, this is fun.
Luckily, I had a boss at thattime, two of them.
And Lois Kern was our officemanager, and I think it's senior

(02:33):
company, Michael Sterns was, andthey hired me.
I just got back into the to doneand came in and.
Hit it outta the park, but I wasbored outta my mind.
Started doing hoteltransactions.
They signed me to an extensionon my contract and I thanked

(02:53):
them by giving them a businessplan and a mission statement on
how I was dreading jettingeverything and moving to
hospitality.
They hid me from corporate for ayear.
So that was truly the biginflection.

Lan Elliott (03:07):
Amazing.
You have changed careers a fewtimes, as you mentioned, first
music and then residential, andthen setting up this hospitality
practice once you made it overto commercial, but continuous
growth.
We know a lot of leaders havecited as a factor.

(03:30):
How do you continue to expandyour knowledge or develop new
skills?

Craig Sullivan (03:37):
I listen and I also try and be creative, like
the sign over my head.
I think creativity to anysituation is a good thing.
Whether it's a conflict or it'sgrowth in your personal and
professional lives or yourbusiness.
I think you need to be creative.
You need to show people thatthere's more than one way to get

(03:59):
something done and do itdiplomatically that way you
don't hear that it ain't broke,don't fix it.
I think that phrase alone buildsin obsolescence in the company
and it starts a downward spiral.
So those are really what drivesme.
I.
I used to sit in meetings, beingvery quiet, paying attention,

(04:23):
never asked a question, soeverybody was out of the room
other than the person I reallywanted to talk to.
And then I would go, Hey, thismay be silly, but I've got a
couple of questions.
Where would you, oh, no problem.
And you could see the wheelsspinning and going, okay, I
hadn't thought about it thatway, but that's a great point.

(04:45):
And then.
I was really pretty introvert.
Okay.
Very quiet.
Didn't, I had one emotion andthat was anger.
It's why isn't this working?
And that was always the crux ofsomething.
After I got to know people,especially on the hotel side,
because I've said this for yearsnow, people in the hospitality

(05:06):
industry are the brightest andbest in commercial.
It's a cash business, realestate.
And, those two items have tomerge to have success.
So it was always about listeningto the attorney.
After all, you get charged quitea bit of money, so let's listen
to them.
It's about the lenders, theinsurance carriers, the

(05:28):
management team, all of youranalysts.
There's so much coming at you.
But all those moving parts makeit fascinating.
And I love spotting patterns,trends.
Trying to get ahead of them.
And I think that's one of themany things that our industry
does better than any other.

Lan Elliott (05:48):
Yeah, we definitely need to do that.
We are basically leasing up ourbusiness every night, so it's a
little bit different than therest of commercial real estate.
So if you're not trackingpatterns it's a big issue.
I'm curious on the idea ofcontinuous growth.
Is there a skill you wish youhad learned earlier?

Craig Sullivan (06:09):
Yes.
Read more data, ask morequestions about the data that's
been presented.

Lan Elliott (06:18):
Yeah.

Craig Sullivan (06:19):
That increase, if you're, I refer to it as pump
and dump.
Okay.
You pump cash into something,prove your performance, then you
dump it.
If you look at it for a longerhold and you look at it as maybe
adjusting your rates and a fewother things, you could actually
make more money in a longerperiod.

(06:42):
But that's not everybody'sstrategy.
A lot of times it's less than a10 year hold, certainly five to
seven.
We're trying to also time it sothat we're not quite at the
crest of the market so that wecan get top dollar and move on
to something else.
Which is a great strategy, butyou also, you really have to
look at, and this is where Ithink a lot of lenders have

(07:03):
problems, which you mentionedjust a second ago.
They don't understand it's a 24hour lease.
They're used to, all thesemulti-year leases on a
commercial asset and they justdon't get it, and they don't
understand how revenuemanagement.
Enhancement plays into it andyou know how you're setting your

(07:24):
average daily rate andeverything else.
So I, those are the things thatI find absolutely fascinating
and the personalities.

Lan Elliott (07:34):
I, yeah, there's much more complexity in hotel
real estate.
I think it's what makes it fun,and I think you find people
looking for that challenge.
Yeah.
I wanted to touch on theadvantages of giving back
because I was recently luckyenough to attend your Click
conference earlier this year,and one thing that you do that's
very unique that I don't see.

(07:56):
Done elsewhere, and maybe thisis the creative part, but you
were very intentional aboutgiving different organizations,
nonprofits, people who aregiving back an opportunity to
share what they're doing withyour audience.
And I'm curious about yourconnection to that and also to

(08:19):
make it such an integral part ofyour conference.
What does that do for you?

Craig Sullivan (08:24):
You know what it does me is it lets me know that
one.
I'm helping an industry that Ilove.
Okay.
That has been very good to theSullivan family and given me not
just a lifestyle, a focus thatno other industry really gave me

(08:46):
gave me the opportunity to raisea beautiful sun and now helping.
Beautiful grandson, and we'vedone a horrible job of
recruiting into our industry.
We're, we've got more boomersgetting ready to retire or
retiring now than at any othertime.

(09:08):
And I'm at the tail end of theBoomer.
Okay.
I'm gonna be 69 later this year,I just say thank you.
I was born into a generationthat I think really screwed
things up.
We, I look at the movie WallStreet and people don't
understand that Gordon Gecko wasthe bad guy, okay?
And everybody thinks and I'm notbagging on our friends at Wall

(09:29):
Street because they're needed,they serve a purpose and all
that.
But you can come intohospitality and be a doorman one
day and be the president of acompany the next.
I don't mean like in 24 hours.
It's a lifetime journey.
You could be a barback andrunning a management company and
some of our leaders that startedout as hourly employees are some

(09:53):
of our best leaders.
'cause they've still got thatingrained in the back of their,
and they're looking out for Ithink we've got the
opportunities to educate,promote, like at no other time
in history.
We take a percentage of our gatefrom the California Lodging
Investment Conference, give itback to our trade associations

(10:14):
in the form of scholarshipdonations.
And, we also do that with crew,commercial real estate women,
and in particular the OrangeCounty chapter California.
And we do invite tradeorganizations to be.
They get a sponsorship level atno charge to them.

(10:36):
They've got the opportunity tohave a table and talk to
everybody.
A lot of them also get up onstage.
I think that messaging isimportant and I think right now,
at no other time if we can starttraining tomorrow's leaders
again this brain trust thatwe're going to lose rather
rapidly.

(10:56):
Is really gonna be unfortunateif that information passed on to
the next couple three.
So it's critically important.

Lan Elliott (11:05):
I love that.
It's a great reason andrationale for being so
intentional in what you do, sothank you for that.

Craig Sullivan (11:13):
Thank you.

Lan Elliott (11:15):
I wanna talk about developing a network because.
I think we're in the greatestindustry, but you get to work
with a lot of different peopleover the course of careers, and
I find because people stay inhospitality for a long time,
that you can actually developfriendships over time.
And we started talking, I thinkat the lodging conference last

(11:38):
year.
We met for the first time.
You just click with people andpeople become friends along the
way and can be relationshipsthat last for decades.
And I know you mentioned thatyou were pretty quiet, which is
hard for me to understand earlyin your career.

Craig Sullivan (11:56):
Yeah.

Lan Elliott (11:56):
But I do think developing a network can be
something that sounds scary topeople.
And I'm curious how you developyour network in a way that's
authentic to you, that works foryou.

Craig Sullivan (12:08):
I believe in networks and it's it's critical
in today's marketplace, nomatter what your field of
endeavors.
But it was listening with theintent of understanding and not
just throwing some randomcomment out.
I think you, you gotta get tothat point.
And you also got to try and lookat the person, not just the

(12:32):
company that.
And the people that I've got thetightest relationships with that
go back to me first getting intohospitality.
And there's a reason I've beeninvolved with and closed$25
billion worth of hotel deal.
Okay.
It's because of knowledge passedis because of relationship.

(12:55):
And two people in particular.
Ani at Westmont Hospitality ismy sister that I never had, and
I love her dearly and she hashad such a huge, and the
direction of my Drew Hardy, thepresident over at 24 7 Hotels is

(13:15):
the younger brother I never had,and he's had a huge impact.
And sometime off camera, I'lltell you about that story.
It.
Our attorneys, our bestattorneys want to get the deal
closed.
And once you start working withthose attorneys, I'm not taking

(13:37):
anything away from othersbecause they all do a great job,
but there's deal attorneys andyou listen and you figure out
their methodology and youincorporate it into your own.
It really is a powerful tool.
And that gets back tonetworking.
Everybody is valuable.

(13:58):
I'm one of the luckiest peopleyou ever meet.
Every one of my clients over theyears are friends.
And you pretty much know prettyquickly if somebody's gonna be
able to bridge that gap betweenbusiness, friendship and the
ones that don't aloha.
I've got other people here that,we help each other.
We also traveled together fromtime to time, not just to

(14:21):
conferences, but on vacations orgoing outta state for a sporting
event.
Things of that nature.
And those are the things thatnot only enrich your career,
they enrich your livelihood andeverything about your personal
life.
Our families are all connected.
They've watched my son grow up.

(14:41):
Okay.
They, I've watched their kidsgrow up.
And it's, it just makes for abetter life.
My life balance, I'm sure mostpeople would say is outta whack,
but, I love what I do.
Okay.
So that's all part of it.
My family will not check into ahotel with me because they know

(15:01):
I'm checking out the hotel.
They want to get checked in andgo to the pool.
But, I enjoy every morning.
Every afternoon, every evening,but it is always about trying to
better one.
If you're resting on yourlaurels, it just doesn't, that's
when progress stops might aswell.

Lan Elliott (15:22):
Yeah.
I love that theme of alwaystrying to get better and
surrounding yourself with peoplewho can help you do that.
And I do think we have the mostincredible people that you can
connect with.
In the course of work, I havesome of my really good friends I
met negotiating across the tablewith them.
Yeah.
And they've become, greatfriends.

(15:43):
You can still do a great job foryour company and hold the line
for what your company needs, butstill also treat the other
person with respect and.
Grace, and hopefully at the endof it you'll be friends
afterwards.
And there's great opportunitiesin our industry,

Craig Sullivan (16:00):
And I think you're absolutely right about
that.
How many deals have been puttogether off market?
People been put together over abreakfast.
Okay.
I don't believe in using thegolf example because that's not
exercise.
It's not that's nonsense.
Okay.
Now all the people that run golfcourses are gonna probably chime
in and tell me differently, butthat's okay.

(16:22):
But over breakfast, we had ahotel here in Newport Beach a
number of years ago that verygood client of mine bought 30
million.
Okay.
And that's what$30 million wasmore like.
He was having breakfast with agentleman that ran a, and in

(16:44):
less than 45 days, he sold it tothis gentleman for 60 million.
Wow.
Okay.

Lan Elliott (16:52):
That's incredible.

Craig Sullivan (16:53):
And the only thing they did from day one to
the day that it closed new beds,new paint, new computers and
operating system, that was it.
That was it.
So return,

Lan Elliott (17:08):
no matter what you do.

Craig Sullivan (17:10):
Yeah.
But that gets back to therelations, and can that grow
into possibly a joint venture?
Yeah, it can.
Yeah.
Because there's a trust level,you still bring your teams in,
you still go through all yourdue diligence and you bring in
your escrow and everything else.
But to have that type ofconnection where, yeah, we

(17:33):
bought this, it was a good pricefor us, we've got plans for it,
but recognizing this other groupcould probably take it to
another level above that, andthey're willing to pay you what
you want.
Yeah.
Let's put the deal together.

Lan Elliott (17:50):
Yeah.

Craig Sullivan (17:50):
And I think we get a lot of that.
It's just that quiet whisper.
The other thing you need to do,you need to be able to keep
things to yourself because ifyou violate that sanctity of
trust, might as well just gosurfing for the rest of your
Okay.
Because you're never gonna getinvolved with a deal.

Lan Elliott (18:12):
Yes, discretion is a really big thing.
You, you had mentioned Doraearlier.
But I wanted to talk more indepth about mentors and
champions because.
When I was younger and I firstgot outta school, I thought, oh,
if you're smart, you can make iton your own, but you really need

(18:33):
people looking out for you.
People who are giving youadvice, or people who are
speaking up for you in thoserooms that you're not in, where
big decisions get made aboutyour career.
And I'd love to hear about howyou've developed mentors and
champions and any advice youhave for others Trying to find
their own,

Craig Sullivan (18:53):
mentors and champions.
Are critical to your successprofessionally, your company's
success.
Professionally, what we all dothe same thing, but what
separates you from the pack?
Okay.
Is it the company you keep?

(19:14):
Is it the advisors that you, isit you, is it the rest of the
team?
I think it's a really uniquehybrid of all of that.
I had a boss that helped me notonly develop a personality and
not be quiet and reserved and Igotta tell you, he unleashed a

(19:37):
monster.
But, if I had an Irish accent,I'd never shut up.
But, it's one of those thingsthat they need to know and care
about you, and you need tounderstand that.
It's not criticism.
They're trying to get you to bethe best version of you so that

(19:57):
you can be successful and gointo it with an open mind.
When I first started working inthe real world, it like you're
lazy.
That I was 20 to 30 yearsyounger than everybody else.
So I got to battle that for along time.
And then, got to the pointwhere, wait a minute, maybe I am

(20:20):
a young Turk and I'm going tochange things.
Change comes with time, but youalso have to have a proven track
record before they start takingit seriously and you're not an
instigator or something else.
So that mentorship and knowingwhen to pull back.
When to say something that's notjudgmental, I think is critical.

(20:44):
That's where your mentors andyour champions is.
Your champions.
You're not in the room, they'redefending you.
They're going, Hey, plan's,right?
Craig's right, so and so isright, and this is why.
And they've been through thesemeetings and this series of
conversations throughout theircareer and their opinion, cold

(21:05):
water.
And it, it, when I worked forpublicly held corporate America,
I firmly believed in an annualreview, even if it did not have
a monetary component.
I wanted to hear what mymanagers, my supervisor, had to
say, and I wanted to see where Icould improve not only myself,

(21:31):
but business and the company.
And those three things I thoughtwere always critical.
And luckily I had a boss thatdid that, and that's when boss
was still a good term.
Okay.
Yeah.
I think tho those are the thingsto focus on and don't take it
personal.
And I used to take everythingpersonal because I used to feel

(21:51):
that my career defined me.
Okay.
It wasn't that I defined mycareer and it took a while and
enough people getting thatthrough me to understand that.
But it's all of your success isgoing to come because of the
people who you around yourself.
It's never, I, it's a team andit may be a personal coach that

(22:16):
you hire for business and life,experiences.
I've done that in the past, andI also had one of my best years
ever where I worked with acoach.
I'm not afraid of takingsuggestions or encouragement or
even, Hey Craig, you screwedthat up.

(22:37):
This is why, because I know it'scoming from a good place and I
know that these people care.
And that's the nice thing aboutmy career and my life.
I've been surrounded by peoplethat you know, not only do I
invite into my home that I wantthem in my place of business, I
want to be in theirs.
I wanna sit down and have a mealwith them.
Everything but golf.

(22:58):
Okay, let's go surfing.
Let's go scuba diving.
We're not playing golf.

Lan Elliott (23:03):
I tried golf, it didn't work for me.
Yeah.
Didn't have good music.
That was my issue with it.
Yeah.
I love I love the idea of reallybuilding those relationships and
being open to feedback.
I think that's one of thehardest things.

Craig Sullivan (23:22):
Yeah.

Lan Elliott (23:22):
To really receive it and understand.
It's someone trying to help you,not someone trying to attack
you.
And it does take a bit.
Of self-assurance and a littlebit of maturity before you're
really able to take it in andmake great use of it.
So thank you.
Thank you for calling that out.

Craig Sullivan (23:42):
I agree.
And you know what?
I probably didn't start maturingtill I was 27, to be all honest
about it.
I think men are bear cubs untilthey're about 27.
They're just all over the place.
Their arms are flailing.
They're yelling abouteverything, and it's me and

(24:03):
this.
And then if you're lucky, youare working with somebody or
you're in a relationship withsomebody, and that light bulb
goes on.
It's not just,

Lan Elliott (24:17):
yeah,

Craig Sullivan (24:18):
it's

Lan Elliott (24:18):
about you and

Craig Sullivan (24:19):
yeah.
Just add alcohol and you knowthe rest, and it's no.
Let's enjoy things, yeah.
But I 27 on, I think that'sprobably the, I, I know for me,
I would not want to go throughmy tool.

(24:40):
I don't know how I made itthrough them.
First off.
But it sounds

Lan Elliott (24:44):
like your twenties were a lot of fun, to be honest,
Craig.
So

Craig Sullivan (24:48):
They were no doubt about it, but wouldn't
wanna revisit that.

Lan Elliott (24:53):
That's maybe a good segue into my question on what
advice would you give to youryounger self, let's say
22-year-old Craig, what wouldyou say to him?

Craig Sullivan (25:07):
Calm down and listen.
Listening is one of your skillsets.
Okay.
The ability to understand and tosurround yourself with the best
people.
I think those are the three thatyou have and a lot of the people
we know have.
And those are skills that willserve not only you, but your

(25:31):
family, your businessassociates, your friends, the
people that you mentor andchampion, in the present and the
future of our industry.
And a lot of industries concernsme and we've gotta be able to
have that ability to advance.
And help them.

Lan Elliott (25:50):
I love that listening has come up a lot of
times and it is one of those, Ithink, really underrated skills.
I remember one time I.
Someone asked me what do you dodifferently?
That is your edge innegotiations?
And I said, I listened.
And they looked at me like I hadtwo heads and I thought, they
don't understand.
Yeah.

(26:10):
But but I think listening,understanding, surrounding
yourself with the best people.
I love being surrounded bypeople who are smarter than me.
So I definitely resonate withthat piece of advice for

Craig Sullivan (26:22):
sure.
I never wanna be the smartestperson in the room.
Okay.
I think everybody on your teamhas a skillset and everybody
does something better than youdo.
Talking about myself.
Okay?
And that's an opportunity tolearn, opportunity to watch

(26:43):
somebody hitting on all eightcylinders and see their drive,
their passion, theirunderstanding, and I cherish
those.

Lan Elliott (26:54):
That's amazing.
Craig, we are coming to the endof our time together.
It always goes really fast whenI'm talking with you, but you've
offered a lot of really greatadvice from your career.
Could you share one final nuggetof advice for our audience who
are looking to advance theircareers?

Craig Sullivan (27:15):
There's never been a better time for
advancement than now, andopportunities are countless.
Be your best self.
Learn.
Listen, understand in threemagic words, please, and thank

(27:38):
you.
Go a long way.

Lan Elliott (27:41):
Amazing advice.
I love that.
Thank you Craig, so much forthis wonderful interview and
thank you for all that you'redoing for our industry, giving
back into the future of ourindustry.
So I really appreciate you beingon everything that you do.

Craig Sullivan (27:59):
Ah, man, this means the world to me.
Thank you so much for invitingme on your show, and can't wait
to see you in person soon at aconference somewhere in the
United States.
Thank you, and we'll have youback on Click Connect soon too.

Lan Elliott (28:14):
Wonderful.
Thank you so much, Craig.
And for our audience, if you'veenjoyed this interview with
Craig, I hope you'll go to ourwebsite, it's personal
stories.com, where you can findmany more interviews with
amazing industry leaders.
Thank you
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

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!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.