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July 31, 2025 30 mins
David Flores Wilson, CFA, CFP®, Managing Partner at Sincerus Advisory, where he helps entrepreneurs, tech professionals, and business owners build and protect their wealth, optimize business exits, and achieve financial freedom.

Named an Investopedia Top 100 Financial Advisor (2019 & 2020), his financial expertise has been featured in CNBC, The New York Times, Kiplinger, and InvestmentNews. A Certified Exit Planning Advisor (CEPA®), he specializes in equity compensation planning, tax- efficient wealth strategies, and strategic philanthropy, ensuring his clients make informed financial decisions that align with their long-term goals. A graduate of UC Berkeley, he holds multiple financial credentials, including CFA, CFP®, AEP®, CEPA®, and CCFC. David represented Guam in the 1996 Atlanta Olympic Games and is an active member of Entrepreneur’s Organization, the Estate Planning Council of NYC, and Advisors in Philanthropy, where he promotes financial literacy and impactful philanthropy.

Passionate about continuous learning and personal growth, David enjoys traveling, reading, Brazilian Jiu-jitsu, yoga, and snowboarding in his free time. 

CONTACT DETAILS Email: dwilson@sincerusadv.com 
Company: Sincerus Advisory
Website: https://sincerusadv.com/

Social Media Address:
LinkedIN - https://www.linkedin.com/in/david-flores-wilson-cfp%C2%AE-cfa-02b5a/
X - https://x.com/NYwealthadvisor

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
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Speaker 1 (01:51):
Welcome, Welcome, Welcome. I hope everyone is having an amazing
day and I am so excited to bring to the
stage today. David Flores Wilson, who is the managing partner
at Sincereus Advisory, helping arch entrepreneurs and tech professionals optimize

(02:13):
business exits and achieve financial freedom, named as investipedia Top
one hundred financial advisor. David's insights are featured in major
publications like CNBC and The New York Times. A former Olympian,
he's passionate about financial literacy, continuous learning and enjoys activities

(02:40):
like Brazilian jujitsu and snowboarding in his free time. Well, welcome, David.
Glad you'd stop by and ready to give us some
education here.

Speaker 2 (02:57):
So I wonderful to be here, Excited for the conversation.

Speaker 1 (03:01):
Yes, indeed, so let's talk a little bit about what
Sincereous Advisory is.

Speaker 2 (03:12):
Sure it's a the only independent financial planning firm based
in New York City, and we work predominantly with business
owners and business founders as well as serial entrepreneurs and
essentially helping them from founding, forming their businesses, to growing

(03:32):
their businesses, to exiting their businesses and beyond, you know,
just trying to be helpful and think about different ways
for them to save money, make money, lower their risk,
and achieve their personal financial goals.

Speaker 1 (03:45):
Okay, so traditional financial planning, why does that fail for
most entrepreneurs.

Speaker 2 (03:54):
Yeah, I mean entrepreneurs are different, right, I think in
a lot of different ways. Many business owners and entrepreneurs.
Retirement isn't uh, you know, they don't fall through the
sort of the pathway of traditional retirement, right. It's you know,
they're don't sort of like hey I'm going to hit
sixty five and and kind of walk away and collective security.

(04:17):
You know, they in general are very passionate about their
businesses and some of them don't want to ever retire, right.
And then you know, and the ones that maybe sell
their businesses, oftentimes we see people going to go back
into into the business world and start a new business.
And so, you know, I think a lot of the
industry financial advisors kind of run around and say, hey,

(04:40):
you know, you need to diversify from your business. You
need to put money to this foll and K cash
balance plan, and oftentimes, you know, we need to slow down, right,
and maybe the business actually has a rate of return
higher than what we could expect in a diversified portfolio,
So maybe it makes sense to kind of go all
in on the business to reinvest. And so really understanding,

(05:03):
you know, what's the rate of return within someone's business
if they hire that extra person, you know, if they
you know, purchase the property in which they operate out of,
you know, they invest in a new project or a
new business line. And so you sort of these traditional
advice around saying hey you should just you know, put
money in some btfs, some mutual funds and then draw

(05:25):
that down. It doesn't work. And so business owners need,
they really need a plan around what is the most
impactful issue in their financial life, which is, you know,
their business, which you know sometimes is you know what
seventy eighty ninety percent of their net worth, and so
having a plan is to potentially monetize that business one day,

(05:48):
you know, whatever their sort of preferences are, whether it's
a succession, whether they want to sell it to employees,
whether they want that business to live on and so, uh,
you know, just really investigating what are the right pathways
and getting owners personally ready, financially ready, and getting the
business ready for any sort of exit planning events can

(06:12):
be so impactful, right, And so that's sort of the
core part of our financial planning for for business owners
because it's you know, we have to address what's going
on in the business and and set them up for
success and so they can accomplish what they want to
do in that you know, with their financial lives.

Speaker 1 (06:32):
Yeah, so that makes sense because everybody is in a
different space and it's getting more intimate with who this
with this person's financial strengths at that time. So I
like that approach. The five Pillars of Wealth for high earners.

(06:53):
Let's talk a little bit.

Speaker 2 (06:54):
About Yeah, I mean, I think when we think about
financial literacy, it's it's such an issue in this country, right,
It's it's not taught in the schools, and people are
are really just kind of learning on their own, whether
it's you know, they're kind of crowdsourcing it from the
people that they know, or maybe you know, they follow
particular financial influencers, you know, cz oormen uh or you

(07:16):
know whoever sort of the you know, influencer of the
day is. And so, you know, oftentimes they're not kind
of getting a comprehensive view of financial planning literacy unless
they really take it upon themselves or they work with
someone really good that they can kind of trust and
really understand their situations. So I think that in general,
you know, financial literacy is a journey, right, it's you know,

(07:38):
people understand that. You know, there's just certain certain things
people can do, right, and so whether it's you know,
the pillars are saving money, they're investing that money, they're
lowering their risk on sort of their assets and their income,
as well as sort of minimizing taxes and managing debt correctly.
I think if if people are doing sort of three

(08:00):
or four of those things at a high level, you know,
they're going to find a lot of financial success and
growing their network over time. But I think the issue
is a you know, it's an ongoing process, right, and
then like really understanding what those fundamentals are in kind
of each of those different areas is so important for
people to grow their wealth, Yes.

Speaker 1 (08:20):
It is, Yes it is, and you know, and teaching
how children to do so at a very young age.
I think is very important because I mean, like myself,
I had the grave of information learn you know from
like you say, Susie and all the other goog gurus

(08:42):
out there, because it wasn't something that was taught in
the household. So with that being said, you know, it
becomes an issue where relationship with money. Do you kind
of help people with their relateationship with finances as well?

Speaker 2 (09:04):
Yeah, I mean to keet it on something super important, right,
that people's experience history and relationship with money cascades through
their lives, right, and so you know, oftentimes it really
just takes you know, and people maybe maybe doing something
really well or not so well, and it's it's sort
of a result of those experiences kind of early in life,

(09:27):
you know, kind of the values that were imparted from
their community and their family, you know, whether intentionally or
not intentionally. Right, and so really understand peeling back the
layers and saying, Okay, what's the money story that someone has?
You know, what were they taught about money? Right? You
know I think that sometimes you know, do they see
money as sort of a you know, with a growth mindset?

(09:50):
Is something that can be used as a tool to
to better their lives and to get them where they
wanted to go. Or is it you know, they see
it as you know, something you know, very finite that
you know and so you know, and you know, there
aren't judgments and sort of either way. But I think
we just have to understand, Okay, well, where are people
coming from? What were the stories that we're told? You know,

(10:12):
how would you know did they have an allowance growing up?
Did they have to work for their money with chores
growing up? Did they you know, what were some of
the lessons they learned? And because it's really impactful because
we sort of guide our clients and advise them on
you know, the spending, on the investing and and how
they make income and how they make decisions with their businesses,

(10:35):
you know, those early formula issues like we mean a lot,
right and so and sometimes uh, you know, we can
think about those things and we can understand the why
and it would help us go forward to make better
decisions in the future.

Speaker 1 (10:51):
So yeah, and that's wonderful because I think that you
do your company does that, because that's where you got
to start. For real, What is your mind set around money.

Speaker 2 (11:02):
Yeah, but people need to I mean it's it's really
alignment right that we need. Right, we need, you know,
because most of the industry is sort of you know
focused on, okay, well, what are people's goals and how
do we kind of get them there in terms of
how we invest and save? But there's this other piece
around values, right, and so goals. Without knowing what we
stand for, what who we are, and what's really important

(11:26):
to us, it can be rudderless. And so finding that
alignment between the values, the goals and then these other
sort of financial activities on saving and spending and investing
and so on, that's super important. Especially, you know, values
and people's goals change over time, and kind of resetting
that and sort of like looking at their financial picture

(11:47):
with the fresh set of eyes is super important.

Speaker 1 (11:50):
Yes, So if people want to work with you, how
do they connect with few? David?

Speaker 2 (11:56):
Sure? You know, people can just google David Floris Wilson
and you know, reach out on our our website, set
up a time to chat. There's some information on our
blog Planning to Wealth as well that you applies to
a lot of business owners as they can kind of
you know, read up on different situations and and see,
uh that could be helpful. But yeah, I love to
love to help out.

Speaker 1 (12:17):
Yes, So legacy beyond wealth, Okay, how do you align
your money with me?

Speaker 2 (12:29):
Yeah, that's that's that's the great question, right, And I
think that you know, I think legacy for many people
and it's different things for different people.

Speaker 1 (12:38):
Right.

Speaker 2 (12:38):
It's I think in the context of people that you know,
in general have kids or you know, have a family,
and how do you want to be remembered right after
someone passes, you know, buy those close to you by
the community. And so that's really you know, when you
cut down to it's like core basic what legacy is, like,

(13:01):
you know, how what are people going to think about
when you're remembered, when your name is brought up and
so and so. For some people it's you know, they
want their kids to think like, oh wow, like you know,
my my parents really uh sacrifice for education and so
and so. You know, the legacy could be that they

(13:24):
paid for education or really encourage education in kind of
different way, whether you know, undergraduate, a grad school or
continuing education. Other people. You know, the legacy could be
you know, having that community. Uh, you know, maybe a
you know, a lake home or or sort of an
actual real estate that sort of you know, family members
can kind of gather and and those stories can be

(13:46):
passed down to the next generation. So I think that,
you know, that's a big part. You know, we both
work mostly with entrepreneurs and business owners in their forties
and so you know, some of them are still just
kind of hitting their stride and and focusing on the growth.
But yeah, it's super also important to kind of take
a step back and say, you know, what is this
all for, Like what do we really want to accomplish,

(14:08):
and what's really important to us? And just you know,
keep asking that question and then you know, let's do
things that can get us there.

Speaker 1 (14:17):
On the on the topic of legacy. Okay, as a
business owner, if you have assets, real estate, things like that,
do you support your clients with shielding that for their children?
For example, yeah, house, you know, right now I'm looking into,

(14:40):
you know, whether a trust fund and learning the different
types of trust funds and how they are handled.

Speaker 2 (14:51):
Yeah, super important, right in terms of like okay, well
you know what's important that business owner and it could
be the next generation, it could be actually the business itself, right,
deserving the name and the and the impact that business
has on the community and the employment and so you know,
how do we do that. And so there's a family
that we're working with right now that there actually a

(15:11):
second generation business owner. You know, it kind of you know,
the first generation the father passed away unexpectedly. Second generation,
you know, it's a little rocky for taking over the business.
And eventually the business is thriving, and so now the
third generation is getting involved and what are the best
practices around that? And so, you know, how do they

(15:33):
get involved and so that way it's a two way street,
and so the business benefits from their involvement and potentially
being the successor to this company as well as uh,
you know, that's that next generation in terms of like,
you know, what's best for them and their career and
their happiness and so, uh, you know, trust structures, tax savings,

(15:53):
these are all integrated into that and sort of you know,
when you kind of work backwards from you know, what's
the bigger picture of what people want toccomplish and then
you know from there, yes, you know what's the most
you know, tax efficient way to do it. I think
when it comes to trust, usually using trust for a
different variety of different reasons. Right, it could be from
tax savings, it could be to avoid probate, it could

(16:17):
be to facilitate the transfer to the next generation, or
potentially even to to add some oversight when assets do transfer,
because you know, the next generation might not be fully
prepared and might not have the financial literacy, and so
you might have some guardrails through the trust structure. And

(16:37):
then you always have to kind of balance, you know,
there's additional costs, you know, potentially you know, there might
be a trustee. You know, there's an extra tax return
every year. Uh, you know, and so uh you know,
always sort of balancing these sort of multi uh factors
when it comes to trying to accomplish legacy, right, and
so uh uh you know, and then you know we're

(17:00):
you know as well, there's there's also an asset protection
part of trust as well that can be super helpful
in protecting against creditors and lawsuits and and things like that.
So yeah, that's all part of sort of that integrated
holistic planning that's super important for business owners.

Speaker 1 (17:18):
Yes, yes, indeed, because as you get older, like you say,
priorities change, you know, thoughts change surrounding you've built something
over time and you want to protect it. Yeah, you
definitely want to protect it for sure.

Speaker 2 (17:35):
Yeah. There's nothing more you know, frustrating and tragic really
than you know, we I've seen this in my own
family that my you know, my grandparents didn't have their
estate plan in place, and uh, you know they're you know,
there are states set in probate for many years, and
you know, they didn't have the right advisors and so

(17:57):
and so. Uh, you know, there was conflict, and you know,
there's all sorts of things that you know, could have
been avoided if with the proper planning. And so you know,
that's really why I'm so committed to this, is that
I've seen it firsthand when it doesn't work well, and
that planning isn't done right.

Speaker 1 (18:15):
Yes, and now in this day and age, you must plan.
You must plan it. Way back in the day, they
didn't have parents, they didn't think like that. You know,
they didn't have the tools. You know, the information wasn't
readily available to them. Ninety percent of the time. The
friends didn't know and the people that they associated with,

(18:39):
so it wasn't even anything they even thought about. So
that's important today, especially today, to protect your assets at
all costs, and you support your clients with trusts and
things like that.

Speaker 2 (18:58):
Yes, and so I think, you know, I think when
it comes to the trust structures, uh, you know, every
state is a little bit different, right, And so we'll collaborate,
of course with the attorneys that will drop those trusts
and and uh, you know, the c pas that will
be kind of signing off. But in general in terms
of you know, sort of the tax strategy and and uh,

(19:19):
you know, making sure that you know, we're minimizing risk
and uh, you know, setting you know, families up for
you know, basically intergenerational success, right, and if there is
sort of inter generational wealth, like, how do we uh
you know, if that's what they want to do, how
do we transfer that in the best way possible with

(19:41):
the least amount of risk and uh and create better
outcomes because frankly as well, you know, you all sort
of see these stories around you know, when wealth gets
transferred from one generation to the other, you know, there
could be lots of unintended consequences. They may not be
ready and uh uh and so yeah, there's a lot

(20:01):
of parents that we work with, and you know, how
do we create that sort of at least minimize bad
outcomes when it comes to uh, you know, commuting, ambition
and so uh, you know, some of these things can
be you know, through the structures, through communication, through some
of the best practices, you can increase the chances of
of of better outcomes. You know, so many family businesses

(20:24):
don't transfer from one generation to the next, and so uh,
you know, a lot of you know, frankly, a lot
of it is uh has to do with sort of
interpersonal conflicts, right, and you know, some of these conflicts
are are foreseeable, right, and so if we address them early,
you know, particularly in the family business, and then uh,

(20:46):
you know, it's it's uh, you know, there's always going
to be a tension between you know, in a family
business where you have owners that are working in the
business versus owners that are not. Right, you know, the
ones that are in the business, you know, they may
I don't want to have just dividends and distributions, right,
They'll they want to reinvest in the business. And yet
from the uh, the perspective of the owners who are

(21:10):
not in the business, it's like, well, you know, this
is this is my legacy, right, like and so I
should you know, I started to participating in the upside.
And so it's you know, there's pushing pool there, and uh,
you know, it's pushing pool between sort of the first
generation and second generation potentially. You know, the first generation
you know has done its certain way and wants to
continue to have control, and yet you know that second

(21:31):
generation might think they're very ready to run with that
business and yet doesn't have you know, they may not
have the full control. And so it's, uh, you're just
being aware of these issues and kind of working through
them over time. Uh is super helpful?

Speaker 1 (21:46):
Yes, yes, because I've seen it seemed like when somebody does,
everybody comes out the woodwork you don't need. You ain't
even tell them, and they found out. The work gets
abrolse so quickly, and when there's you know, something to
be had, it gets it can get really really ugly,

(22:08):
really really ugly. And having what you want in place
up front eliminates all of that.

Speaker 2 (22:17):
Absolutely.

Speaker 1 (22:18):
Yeah, but sure it eliminates all of that. Now, from
spare change to real change. I like that. So giving
giving it why is that so important? I know why
it is, but we want to make sure our audience
it's fully away of the importance of giving strategic.

Speaker 2 (22:38):
Yeah, exactly. I think that, you know, what we try
to do with our clients is that you know, some
often people are are doing reactive giving and so and
then you know, I think a lot of times people
kind of go through you know, almost a life cycle, right.
They might here in NewYork City, you know a lot

(22:59):
of people sort of in their twenties and there, you know,
they might be uh, you know, running the marathon to
raise money for charity and and uh you know, friends
might have a fundraiser here or there, and so they're
just you know, it's like, you know, it's a social thing.
And then you know, they'll have some young kids and
they'll start to shift the giving towards their uh you know,
kids' schools and and uh you know, maybe away from

(23:22):
their alumni or where they went to college. And so
I think we all what we think is important involves
over time, right, And so I think really just bleshing
that out and like, Okay, well you know what's really
important to you and what's the change that you want
to see? You know, is it is it local? Is
it in your community the people you can see around
you kind of uh day to day or is it

(23:44):
you know, it's sort of you know, is it a
health thing that's you know, national and you want to
have an impact that you know is going to make
a difference, or you know, maybe it's you know, something
a little more experimental when it comes to your story,
you are giving you know, you know, a new nonprofit
that's looking at, uh, you know, some of society's problems
a different way. And so we like to have these
conversations with you know, our clients and and kind of

(24:07):
really understand you know, what's important to them, what issues
are important them first and then you know, you know,
and then you know, how should they be giving, you know,
should it be to nonprofit, should it be something more
direct through volunteering. And then as course there's you know,
when we're talking about larger sums, you know, let's think

(24:28):
about how we give in a tax efficient way, right,
and so there's different tax strategies where if you're going
to give x amount, but if you gave it in
a tax efficient way, well then yeah, you'd actually be
able to give more because you're, uh, you know, you're
being tax efficient about it, and uh, and so potentially
there's more impact because of that and so uh and

(24:48):
then how do we sort of monitor that giving? It's
super important say, you know, like is this is this
how we want to be doing it? You know, should
we be changing our approach and kind of going from there,
you know, to go to you know, instead of reactive
giving two more proactive strategic giving is our goal.

Speaker 1 (25:07):
So that sounds like you really really get involved with
your your clients, you know, not just on the finance
spending on where are you you know, what do you
stand for? And that's that's important. Most companies don't do that,
you know, they really don't. They It's like you want

(25:30):
to work with me. I mean, in finance you do
have to know a little bit about a lot about
the money and the assets that they're holding. But to
go as far as you know, mindset and that kind
of thing, that's to me, really caring about your clients.

Speaker 2 (25:49):
I mean, to be honest, it's just it's just fun, right,
It's just uh, it's uh, you know, to be able
to help people in all these kind of different ways.
It's uh, you know, it's why I came into the business.
And you know, every day I get to kind of
see uh, you know the impact of our advice and
you know, whether it's on the investing or on the
philanthropy side, or on their businesses, right, So it's it's

(26:11):
a lot of fun for me. So yeah, I really
enjoy it.

Speaker 1 (26:14):
Yes, yes. And so my last question how to exit
your business without leaving money on the table, because that's
definitely a big thing when you saw your business.

Speaker 2 (26:29):
Yeah, I think when it comes to exit planning, it's
super important to start early, right, And it can seem
so overwhelming for business owners to think about everything they
could be doing on the exit process, right in terms
of you know, getting personally ready, getting financially ready, and
getting the business you know, both ready for any sort
of transition but also more attractive, right. And so I

(26:50):
think that you know, our advice is really to just
start with like very digestible, bite size projects that you
know can help the exit planning process along, you know,
get a business ready, get your finances ready, and so
you know, so often people say, hey, you know, I
want to sell my business, and I want to do it,

(27:12):
you know, in the next six months, and I think
oftentimes you're you're kind of setting yourself up for bad
outcomes and potentially regretting some of the decisions right, and
many of the structures they take a long time to understand.
And so, uh, you know there's things that if we
you know, we talked to people early, we can educate
and put things in place, and so you know, they

(27:33):
can you know, minimize the tax consequences of a sale
or a transition and uh, but not only that, is
that to really make the right decisions right. And I
think so some people kind of go in and say, hey,
I want to sell, you know to a private equity firm,
I want to sell to a strategy buyer. I want
to sell to my my employees, and you know, like

(27:54):
we really want to peel back the layer and say, okay,
why what do you really want to accomplish? And so
sometimes you know, what they think the outcome is going
to be the end up sort of a better outcome
because you know, when you when they see sort of
the pros and cons and the process and so yeah,
at the end of the day, it really just you know,
if they can start early and start that planning early,

(28:17):
you know, they can really uh, you have a good
outcome and not leave money on the table. For sure.

Speaker 1 (28:23):
Yeah, so it sounds like your company doesn't miss a beat,
you know, it's just you make sure that you cover
everything with your client because sometimes we don't know, we
don't know, and you know, talking it out with a
professional that knows the engine out can make a world

(28:43):
of difference for clarity with your clarity being clear on
and that one question that you just said, why do
you want to do it?

Speaker 2 (28:55):
That why?

Speaker 1 (28:56):
Yeah, that that's crucial. No matter what you do, you
need to know your.

Speaker 2 (29:01):
Why exactly exactly. No, it's you know, like it's sort
of two wives too right, It's it's sort of why
did you? You know, from a business owner's perspective, it's like,
you know, why did you start the business? And you
know what's the why actually about exiting your business too right?
Is it to spend more time with family, Is it
to uh, just to down shift and enjoy yourself. Is

(29:25):
it to work on other projects? This is to you know,
to make more of an impact in the community, you know,
with volunteering or contributions to charities, and so you know
that why is super important?

Speaker 1 (29:37):
Yes, absolutely so, David. Again, how do people connect with you?

Speaker 2 (29:44):
Yeah? People, can you find me on on the website
at Sincerius ad V. Dot com or you know, comes
up if you just google my name David Floris Wilson
instead of time to chat.

Speaker 1 (29:54):
So yeah, indeed, well I've gotten a lot out of
this conversation because I'm at that place where I'm planning
some things and this conversation was very valuable to me,
and I'm definitely looking forward to more information in terms
of my goals going forward. So I thank you for

(30:17):
all that you do and for sharing with us and audience.
We thank you as well for stopping by.

Speaker 2 (30:24):
Thank you so much.

Speaker 1 (30:27):
Thank you to our guests and you our value audience.

Speaker 2 (30:33):
Let's stop you by.

Speaker 1 (30:35):
We truly appreciate you. Many blessings to you and yours
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