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June 13, 2025 26 mins

Cut The Tie Podcast with Thomas Helfrich
Episode 262

In this introspective and powerful episode of Cut the Tie, Thomas sits down with David Steele—entrepreneur, investor, restaurateur, and founder of One Wealth Advisors—to unpack a career built on service, reinvention, and emotional intelligence. From growing up poor to managing over $1.1 billion in client assets, David shares the lessons behind every scar, including why he walked away from Bear Stearns and how failure in one restaurant birthed a booming hospitality empire.

David also opens up about choosing not to have children and how a life of intentional service shaped his purpose beyond money, homes, or success.

About David Steele:
David Steele is the founder and CEO of One Wealth Advisors, a boutique financial planning firm with over $1.1 billion in assets under management. He’s also the executive chairman of a thriving hospitality group responsible for one of the most successful restaurants in San Francisco history. From financial planning to food, David believes that every business should be built to last—and built in the service of others.


In this episode, Thomas and David discuss:

  • Rebuilding From Nothing
    From being fired, betrayed, and surviving Bear Stearns, David shares how he kept starting over—and how each reset sharpened his mastery.
  • From Finance to Food
    Why he opened a restaurant “to scratch an itch,” and how it became an award-winning brand with multiple locations and CPG growth.
  • Scar Tissue as Strategy
    The biggest lessons weren’t from wins—but from the pivots, setbacks, and imperfections he couldn’t ignore.
  • The House That Didn’t Make Him Happy
    David built a modernist dream home—then realized joy lived in a tiny New York apartment.
  • Mastery, Not Monetization
    David explains why every business he starts is built for longevity, not a quick exit—and why he’d rather keep his business partners than cash a check.

 

Key Takeaways:

  • Starting over is not the same as starting from zero
  • Relationships are the most valuable asset you can build
  • Your art doesn’t have to be traditional—business can be your medium
  • Don’t chase “more”; chase meaning
  • Everything we do should be in service to others


Connect with David Steele:
🔗 Website:
https://davidsteele.xyz

Connect with Thomas Helfrich:
 🐦 Twitter:
https://twitter.com/thelfrich
📘 Facebook: https://www.facebook.com/groups/cutthetie/
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich/
🌐 Website: https://www.cutthetie.com/
📧 Email: t@instantlyrelevant.com
🚀 InstantlyRelevant.com



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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to Cut the Tie podcast.
Hi, I'm your host, ThomasHelfrich, and I smell lovely.
Today.
It has nothing to do with ourshow, but we're here to help you
cut a tie to anything holdingyou back from success, and I'm
joined today by David Steele.
David, how are you today?

Speaker 2 (00:13):
I'm great, thank you.

Speaker 1 (00:15):
It's nice to see you.
You were talking off camera.
You got multiple homes.
You start these companies.
You're successful.
Life is good.
You got all your hair.
Why don't you introduceyourself and what you do?

Speaker 2 (00:27):
Well, professionally, let's see.
I am the founder and CEO of afinancial planning company
called One Wealth Advisors.
I started the practice 34-ishyears ago and we manage about
$1.1 billion in assets for about380 clients and it's a lovely
little partnership, family typebusiness.

(00:48):
And then about 15 years ago Ihad an itch I needed to scratch
and open a restaurant, so I puta team together to open a
restaurant.
It ended up being one of themore successful restaurants in
the history of San Francisco andwe turned that into a company.
And now I'm essentiallyresponsible for having started a

(01:09):
company that has eightrestaurants and the consumer
baggage goods business and I'mfounder and executive chairman
of that company.

Speaker 1 (01:18):
When it seems like is your?
Is your goal entrepreneurshiplike world domination, or do you
come up with an idea andopportunities go with it?

Speaker 2 (01:27):
Well, there was who I was years ago and who I am now.
So goal future tense is to helppeople live their dreams and
achieve their goals.
Because I've achieved all of mypersonal, professional and,
frankly, personal goals as well,and I think that things are not

(01:48):
worth doing if they're not inthe service of others once one
satisfies their base needs ofstaying warm, dry and fed.
And so, having written multiplelife plans maybe every decade
and having achieved everythingin each of those little life
plans I did, I had an awarenessthat I now want to help other

(02:11):
achieve their life goals andactually write life plans.

Speaker 1 (02:16):
So I hear that I feel like you didn't challenge
yourself enough.
You hit all the goals.
I feel like there should be afew on there.
You're like, oops, missed them.

Speaker 2 (02:23):
Maybe, but I'll just push back and unpack that a
little bit.
It's like I I have heard thesaying that happiness is when
your reality exceeds yourexpectations, and I think at
some point time you can letyourself be happy yeah, I'm in
that phase where I'm like I lookat the house, I've never been a
car, so that's an easy one.

Speaker 1 (02:44):
I have a comical car of beat up minivan that I just I
love because I don't give ashit about it, which is the best
.
But then I see, like thetrophies you collect in life,
like right, people have cars,they have houses.
At some point I'm like I wantto have less and want less.

Speaker 2 (03:21):
How do you ever look at it and go of my life savings
into this home and all I see isimperfection when I walk through
the home, having tried to plana perfect home.
People walk up to this home andthey say it's arguably the most
beautiful home anybody's everseen.
And I have a 350 square footapartment in New York City that

(03:43):
I also live in sometime.
I'm absolutely happier when I'min that little apartment in New
York than when I'm in this homeseeing nothing but problems.
Still, I couldn't help myself.
I had the money.
I knew at some point in my lifeI wanted to build a home.
I wanted to see if I could doit design it from ground up with
an architect.
I did.
Lo and behold, the journey wasvery painful and the the result

(04:07):
is is disappointing.
And so what a life lesson youknow, did you?

Speaker 1 (04:13):
uh, are you the only one that like sees it?
So, to give you an example,I'll do my own like kind of home
repair, tile work, wood,everything except everything
except working a hot electricalpanel.
I usually bring an electricianto do that.
I'll do everything, though Iwon't install a panel though,
cause that's like, that's likeyou messed that one up.
It's death instantly.
But um, I look and I can seeall the little nooks and
crannies of all the stuff that'swrong, but no one else notices

(04:34):
at all, cause they couldn't.
They couldn't know the detailof what it could have been.
Do you suffer from the same?

Speaker 2 (04:41):
Yeah, but not for the same reason.
I don't do any of my own work.
To me, my philosophy, andpretty much anything I do in my
life, is, if I can get somebodyelse to do it 80% as well as I
could and I can quality controlit up to 100%, I just save
myself a heck of a lot of time,and that certainly pertains to
the type of work you justdescribed.
So I see all the imperfectionsbecause of God knows that

(05:05):
psychoanalytically richterritory and I'm sure that my
therapist would have a lot tosay about that but it's because
I'm OCD and not because I didthe work myself.
On himself critical.

Speaker 1 (05:17):
That's what we're getting into.
We're just getting to set upthe ties you had to cut in life.
So, on your journey, a massivesuccess by anybody's means, and
you can always, you could alwayshave more, want more, do more
in your life, but by allmeasurable accounts you're very
successful.
But what's been the biggest tieyou've had a cut to get there.
I mean a lot.

Speaker 2 (05:38):
Let's see.
I mean I grew up poor my mom,single, single parent, two
children, school teacher.
We had no money.
I had to work from 16 to 24 inrestaurants, dishwasher up to
manager, got out, startedbuilding a financial planning
practice, which is anexaggeration.

(06:00):
It was a stockbroker practicewhere I really didn't know what
the hell I was doing, didnothing but lose clients' money
because I didn't know what thehell I was doing and had to
start over and rebuild mybusiness over and over and over
again.
But I was very disciplined andI had a lot of systematic
behavior around that.
And then I actually got firedfrom the CEO of a financial

(06:22):
finance company, hated me, had areason to fire me, fired me,
had some partners that kind ofscrewed me over, had to start
over again after having built adecent little business five
years into my practice.
And then I was with BearStearns, which went out of
business, essentially in thecredit crisis, and we were
bought by JP Morgan, which mademe and my partners miserable,

(06:47):
and we had to leave JP Morgan tostart our own company, which
was scary, but I don't know.
I think that would be definingcutting your tie, and it was a
bold move and it obviously paidoff.
But these are inflection pointswhich, for some people, would
possibly have had them thinkabout pivoting careers giving up

(07:10):
, if you will and I just thinkthat those moments in time are
really what defines us.

Speaker 1 (07:19):
Well, you look at them, it looks like not as a
failure but as a lesson.
Ah, I learned something, let'sdo that different.
I learned something, let's doit again.
And if you get so married on anidea, like the OCD on an idea,
and you just cannot get awayfrom it, then, yeah, that idea
will probably fail.
But you also created that ideawith the least amount of
knowledge in your life at thatmoment, and so it's like you
have to adapt, otherwise You'renot learning from the knowledge

(07:41):
that's being presented to you insuccess or challenge.

Speaker 2 (07:46):
I mean, I read Malcolm Gladwell has this idea
of 10,000 hours is at.
That moment in time is when youhave developed mastery in a
thing.
For me it was survival.
I didn't know I was developingmy 10,000 hours and I should

(08:12):
just stick with it.
I just thought the path ofleast resistance was to actually
continue to do what I knew andknew best, even though I was
starting over.
Upon reflection I was buildingmy 10,000 hours, so it was much
easier for me to rebuild eachtime I had to rebuild.
Then probably somebody coming tothe business that was leaving a
different business because theywere pivoting, because they
failed and they had to startover to literally learn the
business from ground up.
You know, interestingly, I hada restaurant in San Francisco

(08:34):
that failed and the chef, whohas had equity in the business,
um, was thinking about leavingthe business and going to start
to be a foreman on his uncle'sconstruction company.
And I told him that's fine ifyou do that, it's your choice
and I can't tell you not to dothat.
But I will tell you you havedeveloped mastery in this thing

(08:56):
and it's failed right now.
So you think you're at zero,but the truth of the matter is
you're not really at zero.
You're not really at zero.
You're at a huge competitiveadvantage versus anybody else
who is starting out in therestaurant business or, more
specifically, starting out as anowner.
You've been an owner, you've hada failure and there's a real
opportunity for you to pivotthat into something in the

(09:18):
future and to apply that mastery.
Lo and behold, I convinced himto open another restaurant.
The restaurant is one of one ofour more successful restaurants
, radically successful, and he'she's an equity holder, and then
he owns equity and the secondrestaurant that we opened with
him, and so and we're literallytoday talking about doing a

(09:40):
third and he's making a lot ofmoney, he's by just bought a
house with his wife and newchild, and that was an
inflection point for him, and Isuppose it was only because I
had gone through thoseinflection, going through those
inflection points, and chose notto leave and chose to apply my
mastery that I didn't know I hadat the time.

Speaker 1 (10:01):
Do you?
I'm sure you have lots ofmoments, but do you have a
moment that sticks with youwhere you realized, like the
epiphany ah, I'm going to startor stop doing this or that.

Speaker 2 (10:13):
I don't stop doing much.
I have started doing somethings, more than a couple,
which I guess relates to what wewere just talking about,
because once I've sort offigured something out well,
actually I'm going to pull backon that.
I wrote a play.
It was on stage, Thought Iwanted to be a writer, Decided I
hated writing.
I didn't enjoy it.
I had several shows with someof my art visual art in art

(10:38):
galleries, sold some work,realized I actually didn't like
creating the art.
I thought I would like creatingthe art and I actually was
decent at it, but I didn't enjoyit and had a realization from
those experiences that my art isliving, breathing art, which is
, as an entrepreneur, startingbusinesses and I believe those

(11:00):
are rightfully, you coulddescribe them as art projects in
the way I think of as art.
So I guess there have beenthings that I've started and
then stopped doing.
So, yeah, I mean, but for themost part, the businesses I've
started.
I haven't built businesses tosell.
I've built businesses that arehopefully generational and I

(11:21):
just sort of keep doing them anditerate within.

Speaker 1 (11:26):
Yeah, I think that's probably why you build a
successful business, because youbuild with the idea for
existence and so it's got tohave something special,
something that keeps peoplecoming back, something that
you'd be proud of.
And when you build something toexit, you're building it for
more efficiency and market andmoney, and those don't always
line up to the experience of thecustomer.
Is it fair enough to say that?

Speaker 2 (11:46):
well, the way I, the way I see my business life, my
professional life, is.
It is the different companiesthat I started that I am still
involved with, and there's morethan a couple.
If I were to sell them, I wouldno longer get to have the
relationships that I have withmy business partners.

(12:07):
Business partners and the ideaof getting money but losing
those relationships, therichness of those relationships
and how they impact my life andmy happiness, would be really
heartbreaking for me.
So my motivation may be alittle bit different.
I do believe any business thatone can sell for high valuation,

(12:31):
any traditional business I'mnot talking about a venture
capital backed business thatreally isn't built to develop
positive cash flow and besustainable over time it's
really trying to fill a quickniche that they believe would
fit into a potential acquirer.
A technological gap would beappealing to potential acquirer.

(12:53):
A technological gap would beappealing to an acquirer, and
that really is the genesis orthe purpose of starting the
business.
Those exist and I'm sure peoplemake lots and lots of money.
But most businesses that arestarted are, I believe, started
because the person had an ideaand they wanted to make some
money for themselves and theywanted to build it and keep
growing because they wanted tomake some money for themselves.
And they wanted to build it andkeep growing because they

(13:14):
wanted to make more money.
They wanted it to be, theywanted to have confidence that
it would sustain.
Oh, and then they woke up oneday and said oh, there's a buyer
.
I'm tired, I'm going to sell it.
I have no problem with thatdecision.
It's fine.
Who knows, maybe someday I'llsell a business.
But I think the motivation ofstarting any business the way I
see the world is you shouldimagine it living for

(13:36):
generations after you're dead.
And if you do that, then yourdecision-making, first of all,
you're going to make long-termversus short-term decisions.
You're probably going to befiscally responsible.
Every dollar you spend you'regoing to see as an investment in
something that's going to havea return on investment long-term
return on investment.
It's just a different type ofmindset.
That has been my mindset.

(13:58):
Just so happens, I woke up oneday and realized, man, I love my
relationships with my businesspart.
This is really one of the greataspects of my life and if I
were to sell these things itwould be heartbreaking my life
and if I were to sell thesethings it would be then
heartbreaking yeah, it's likeit's your family, almost it's a.

Speaker 1 (14:16):
Yeah, what impact it is, and so, and so I and you've
talked about this a little bit.
I normally ask what kind ofimpact it's had on your life to
be the way you are, but maybedescribe the impact you've had
on other people's lives buildingthese businesses that you've
played so good to they're nothere to speak for themselves, so
I'm going to attempt to speakfor them.

Speaker 2 (14:31):
I think they would say that for the most part, the
the partners that I have in mybusiness would say that their
lives are better because I'vebeen involved with them, that
they may not have been able toaccomplish anything near what
we've been able to accomplishbecause I've been an influence

(14:53):
on our entrepreneurial spirit,our boldness, our strategic
thinking, and that I havebecause of my view on how to
work with people and buildbusinesses.
It's, it's a, it's an activeempowerment for them.
That is, they feel moreempowered and more successful by
all measures because I've beentheir partner.

(15:15):
But I absolutely have gottenmore from it than they have,
because my sense of purpose iscompletely predicated on my
ability to positively influencethem.
And I got a text from one of mypartners in one of my companies.
He's the CEO of one of mycompanies that he and I started
and he texted me and said I justwant you to know that outside

(15:37):
of my parents, there's nobody inmy life who has been more
supportive and more positive andinfluential than you.
I mean I, I I teared up when Igot that.
He did.
He literally said that to meyesterday, that text from him.
He was 24 when I hired him andthen made him a partner, and

(16:00):
he's 40 now and he's the CEO ofthat company and I'm executive
chairman of that company.
We're partners, we run thecompany together.
He does most of the artwork,though, and what a?
I mean I mean that that rightthere.

Speaker 1 (16:13):
Honestly, that text was worth a million dollars,
worth something crazy like thatto me yeah, I'm one who believes
that you don't separating workand life, and you just can't,
and your identity is wrapped upin both and it's a cop-out.
You'd be living two differentlives.
Yeah, you'd be living twodifferent lives.
Yeah, you'd be living twodifferent lives.

Speaker 2 (16:31):
It's a cop out, it's.
I believe that anybody who says, oh, it's just business, um, I
don't want to do business withyou.

Speaker 1 (16:39):
Yeah, I mean, I get that and I agree with you.
Like it's just too interrelatedto say it otherwise.
And anybody who's thinking, oh,I just go to work and I just
want to be home, well, youshould probably get out of what
you're doing, because you'rejust trading your time and soul
for money.
So you might as well try tofind purpose if you can At least
take a direction toward it.
Anyway, we could go do a whole,probably podcast on that, like
a whole series.

(17:00):
Tell me something, just give alesson to the listener.
If anybody listening out therethey're on an entrepreneurial
journey.
What's the best thing?

Speaker 2 (17:23):
Give.
Give them some advice.
I said it earlier and I can'temphasize this enough Everything
we do should be in the serviceof others, assuming hour, every
day, everything they're doing,and just make sure that it's in
the service of others.
It doesn't mean you shouldn'tget paid for providing such a
service.
In fact, usually you should,and I think there is some

(17:45):
wrongful guilt around conflatingbeing compensated for serving.
There's nothing wrong with that.
But I'm in the service of theclients of my financial planning
company.
I'm in the service of my teammembers of that company, of my
partners of that company, everysecond of the day, and the same

(18:06):
thing with my restaurant company.
I'm in the service of thecustomers that walk through the
door.
I'm in the service of the teammembers, the partners in the
company, the executive team.
We are in the service of theemployees.
I can go on and on and on.
It is truly all about service.
Oh and, by the way, I get paidpretty well.

Speaker 1 (18:25):
Yeah, I like that.
That's a good idea.
All right, let's do some rapidfire.
I'm curious in these, who givesyou inspiration?

Speaker 2 (18:34):
My mother.
She taught me aboutrelationships.
She taught me about how, really, at the end of the day, all
human beings want is to be lovedand valued.
And one of the ways that wefeel loved and valued is by
loving and valuing others andhaving it be reciprocal.
And sometimes you have to endrelationships where it's not

(18:56):
reciprocated, but that doesn'tmean you stop doing that, and
she taught me that and that wasthat's really probably the
fundamental reason for mysuccess.

Speaker 1 (19:07):
Yeah.

Speaker 2 (19:08):
I hope my kids say something about me like that Me
too.

Speaker 1 (19:13):
What's the best business advice you've ever
received?

Speaker 2 (19:28):
it's there.
There is a healthy tensionbetween hurry up and slow down,
that is, to making snapdecisions versus being
deliberate.
And so when one is in thebusiness world thinking about
projections or goals or behavior, systematic behaviors, I think
one at all times needs to feelcomfortable and uncomfortable.

(19:49):
And that tension is a goodtension.
And you know, you've heardpeople around goal setting,
which is, whatever goals youhave, make sure and you said it
earlier, right, did you?
Did you challenge yourselfenough?
Right?
And I think my pushback was atsome point in time you have to,
you have to be happy and it'sokay to be happy.
And what I'm arguing for isthat that tension, that push

(20:12):
pull is, is very healthy, and toto harness that and respect
that.
And if it's out of whackthere's probably a problem.
And having it, having equal orequilibrium between those two
seemingly oppositions, is a goodthing.

Speaker 1 (20:29):
What's that?
A must read book.

Speaker 2 (20:33):
Oh man, wow, must read book.
Uh, I'm drawing a blank, butWarren Buffett read a book that
is the basis of his entirecareer by Benjamin Graham, and I
think it's the IntelligentInvestor.
For me, that book is a bookthat teaches you to try to

(20:59):
remove emotion from yourdecision making and really look
at the facts, the fundamentalsof things, because the world can
be very you know, especiallyright now with what's happening
in the financial markets andtariffs and political
environment, etc.
It would easily lead you tomake emotional decisions and I

(21:23):
read that book back in the 90sand it really stayed with me
that try to push aside all ofthe noise and really make
fundamental, foundational,analytical decisions, rather
than emotional ones.

Speaker 1 (21:34):
That's solid advice.
Also, just compound interest,start early.
It's a simple one.
If you had to start over and ifyou had to go start over, when
would you start over and whatwould you do differently?

Speaker 2 (21:45):
Meaning at what point in my life would I have chosen
to start over?
Upon reflection?
Correct, that's a really goodquestion.
I think for me I was reallyready to rock and roll in my 30s
because I had learned a lot, Ihad matured in my 20s, and it
took a lot of tie cuttingfailures, wins, losses, scar

(22:09):
tissue development to then havemore clarity about what my
capabilities were.
So I think it would have beenin my 30s.
Does that answer your question?
I'm not sure it totally does,though.

Speaker 1 (22:20):
Well, it's win, but what would you do differently?

Speaker 2 (22:22):
Oh, what would I do differently?
Well, I would have started myown company and I was with Bear
Stearns and then JP Morgan foryears and I would have looked at
the fact that I was building ateam within a large organization
, and then what that largeorganization was providing me

(22:44):
was completely dependent upon mebeing afraid to leaving them,
and that I needed them when intruth, I didn't need them, and
that everything they wereproviding me was easily
attainable on my own.

Speaker 1 (22:57):
Awesome.
If there was one question Ishould have asked you today, but
didn't, what would thatquestion be and how would you
answer it?

Speaker 2 (23:05):
Well, as I've looked, you know, dug into your podcast
a little bit and we had talked.
I know that you attempt to getto more vulnerable places with
people, and so I think I wouldhave asked, asked me, why I
chose not to have kids Go ahead.

Speaker 1 (23:18):
You have to answer your own question, and so I
think I would have asked me whyI chose not to have kids Go
ahead.
You have to answer your ownquestion.

Speaker 2 (23:22):
I think I chose not to have kids because I saw my
mom struggle so hard withraising my brother and I on
teacher salary, no money havingbeen left by my father, and it
really put her into a dark, dark, dark place.
And I was nine years old and Iobserved that and I think that

(23:46):
really had an imprint on me.
To say that having kids is suchan incredible struggle that it
seems like without kids it wouldbe less of a struggle.
I have observed excuse me, I'veobserved many of my clients
have incredibly happy,harmonious families and what

(24:08):
amazing humans they are, theentire family as they get
together and sometimes I look atthem like they're aliens.
I just don't.
I just don't understand.

Speaker 1 (24:20):
I just don't.
I just don't understand.
Yeah, it's the pain.
The pain of having being thechild on the other end of that
is the pain you don't ever wantto.
You'd have to relive it almostas kids.
It would be hard, but you'd beproviding for them.
I have a feeling you'd probablybe a pretty good dad.
I don't know.
I think you probably Maybe.

Speaker 2 (24:36):
Thank you, and I do want to say that intellectually,
I think you know, and I do wantto say that intellectually, I
think you know.
I think there's nothing wrongwith people getting divorced

(24:57):
Nothing, it's how does thedivorce happen, Right, Is there
the kids?
The kids just want to be loved,'t able to provide that to us,
and so all I saw was dysfunctionand struggle.
So it was.
I don't think it was.
I don't want anybody to leavethis to me thinking I said don't
get divorced, stay togethereven if you're miserable.

(25:17):
Because I'm most certainly notsaying that.

Speaker 1 (25:21):
I appreciate that.
Thank you, I appreciate youcoming on today.
By the way, shameless plug timeIf who should get ahold of you
and how do they do?

Speaker 2 (25:28):
that you know I, I a lot of people go on podcasts, I
think because they're doing somebusiness, some form of business
development.
Truthfully, I just I don't wantto write a book, but I think I
have a lot to say.
So I like to talk and that'swhy I choose to go on podcasts
and tell my story.
But you can.
I have this silly website,david Steele, d-a-v-i-d,
s-t-e-e-l-e, dot X, y, z.

(25:48):
That shows that you couldprobably reach me at and it
shows you my weird background.

Speaker 1 (25:55):
Wonderful, I love it.
You don't even sound, just I'mout here just telling my story.
I love that.
Yeah, true service-orientedarchitecture of a brain right
there.
I love it.
Altruism in its purest form.
Thank you, by the way, forcoming on, david.

Speaker 2 (26:07):
Yeah, thank you for having me.

Speaker 1 (26:09):
For everyone who's still listening.
I appreciate you Go out there,cut a tie to something holding
you back from success One thingyou should probably do.
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