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August 27, 2025 32 mins

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Gene Natali, CFA, joins us to discuss his mission to solve America's financial literacy crisis through his innovative platform Troutwood and his bestselling book "The Missing Semester." We explore how technology can scale financial education and planning to reach millions of Americans who lack basic financial knowledge despite good jobs and education.

• Gene's journey from institutional asset management to becoming a financial literacy champion
• The inspiration behind "The Missing Semester" which has reached over one million readers
• How Troutwood's platform connects planning, engagement and incentives in one unified system
• The $14 trillion retirement shortfall in America and how the finance industry has failed average Americans
• Why financial education must focus on action rather than just knowledge
• The importance of secure AI in maintaining trust in financial guidance
• Community connection to investing makes financial markets more relatable
• The need for financial habits to become as automatic as brushing your teeth
• Why the "delta" (taking action vs doing nothing) matters more than "alpha" (investment outperformance)
• Creating centers of excellence for financial literacy across institutions

Help someone you know who's having financial challenges by sharing Troutwood's tools with them. If everyone reaches out to two or three people, we can start to make a real difference!

https://www.troutwood.com/troutwood-basic


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Disclaimer - These podcasts are not intended as investment advice. Individuals please consult your own investment, tax and legal advisors. They provide these insights for educational purposes only.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Steve Davenport (00:02):
Hello everybody and welcome to Skeptic's Guide
to Investing.
Today I'm very excited to havemy good friend and fellow CFA,
Gene Natali.
Gene is, Mr.
Financial Literacy.
He's been working for the last15 plus years in this space.
He was cutting edge when hecame out with a book called

(00:26):
Missing Semester, which talkedabout how everyone's education
is missing one semester where wefocus on personal finance and
investing.
Everybody should have theability to succeed financially
and I believe what Gene is doingwith Troutwood and other things
, um, Troutwood is theapplication that he's developed

(00:48):
and built with his team and Ithink what he's doing and what
he's done, um, is a great storyof American ingenuity.
I believe that we uh, you know,we all have a journey and we
all get started somewhere.
So, as I Gene, I'd love him totalk a little bit about where

(01:08):
this desire and drive forfinancial literacy came from and
you know, I don't think it'sany different than where you
know it came from from a lot ofpeople who are creative and
energetic.
But I'd love to hear, Gene,just a little bit about your
financial journey and how youstarted.

Gene Natali (01:29):
Steve, thank you for that introduction and for
the friendship.
It's hard to believe we'veknown each other as long as we
have now, but I'll doubt it,accidents happen.

Steve Davenport (01:39):
A Steeler fan and a Patriots fan can coexist.

Gene Natali (01:43):
Absolutely and make each other stronger.
So I appreciate theintroduction.
We are 100% aligned on everyonedeserving equal financial
opportunity, but entering thatplaying field from different
backgrounds and different pointsof life, and I think that's
been one of the historicalchallenges.
Your specific question was whatwas where my drive for this

(02:04):
topic came from.
I'll share a very short biointroduction while answering
that question.
I grew up in institutional assetmanagement, so after college I
entered in excuse meinstitutional sales, spent close
to two decades getting to knowhow large pension funds, large

(02:24):
financial institutions, largeendowments invested their
capital and planned for thefuture.
Simultaneously, I took aninterest in personal finance
based on experiences I had whileattending Carnegie Mellon
University's Tepper School ofBusiness, seeing brilliant minds

(02:45):
navigate this very difficultcurriculum, become real-world
decision makers, but at no pointin their careers being taught
the basics.
We could graduate students whocould do complex option modeling
, massive debt and bigmisunderstandings of what that
meant.
Yeah, massive debt and bigmisunderstandings of what that

(03:18):
meant.
So the title for the book thatyou alluded to, the Missing
Semester, was very catchy at thetime.
There's a lot of good workbeing done across the country.
If I wrote it today, I'dprobably have to retitle the
Missing Semester.
Personal opinion that I wasn'ttaught this stuff or I was
ignored.
It was looking at folks intheir thirties and forties who,
steve, despite great jobs andgreat educations, were living
paycheck to paycheck becausethey hadn't been taught this
subject.

Steve Davenport (03:35):
Yeah, no, I, I, I think it's sad and I I've,
I've looked at this and you knowI've always given you the
analogy that it feels like withfinancial literacy we're just
trying to put out a forest firewith a garden hose.
What you're doing isinspirational in terms of you

(03:55):
saw a problem, you saw a needand then you went after trying
to solve it.
I'm trying to solve it and Imean I'd love to you know, hear
more about the.
You know you had a second bookright after Missing Semester and

(04:17):
Troutwood and how it gotstarted and I mean I think our
listeners would love to.
Everybody wants to start a newAI company.
You were, you know, kind of inthe forefront of trying to use
technology to help people and Ithink it's a great story.
Tell me about Troutwood.

Gene Natali (04:32):
Absolutely, and I love your garden hose analogy,
steve.
We have a $14 trillionretirement shortfall in America.
The finance industry has failedthe average American.
I'm generalizing with thatstatement, no, I think you're
accurate.

Steve Davenport (04:48):
First of all, we're just now getting to the
point where we have 401ks forall.
I mean, if the pensions wentaway 20 years ago, why now are
we giving people at the lowereconomic levels an ability to
save in a 401k?
And it takes 30 years torealize that this is a problem

(05:13):
for everyone.
Retirements are not funded bypensions anymore.
It was a time, and those daysare gone, and nowadays are 401ks
.
But this is a 70s developmentand we're just now getting to
the point where I think we cansay that everyone has
availability of a 401k, which isnice, but now we're going to

(05:38):
start to put crypto and privateequity in them.
I think that we need to helppeople, and I don't know where
you think the greatest need is.
We can maybe talk about that ina little while, but in this 30
minutes I want to get peoplesome help and I think that I

(05:59):
will include whatever links toyour materials and ideas that
you would like, but just tell usa little bit about what
Troutwood tries to do, because Iknow the app from five years
ago.
I don't know exactly how longyou've been doing it.

Gene Natali (06:17):
Yeah, about five years to touch longer.
You are correct, steve, thataccessibility is being solved
for speed.
We're not moving fast enough asan industry.
White label IRAs are apossibility and we're not
running to them.
My understanding, my belief andthe principle for founding
Troutwood is we were lacking acohesive and connected planning,

(06:42):
engagement and incentiveplatform.
Connected planning, engagementand incentive platform we built
a platform that, throughtechnology, will allow financial
advisors and financialinstitutions to seamlessly and
frictionlessly scale theirbusiness, their practice,
through technology, whileinviting their customers and
their prospects and their nextgeneration into a platform that

(07:03):
makes communication and guidanceeasy.
That's a very high-level summary.
Let me go one step back thoughhow and why the missing semester
has crossed over a millionreaders.
I am extremely proud of that.
I keep that quiet.
I've never posted that on asocial platform, but I almost

(07:23):
made a mistake with the, thebook and that same mistake
almost made a troutwood.
So consider me a slow learner.
But when I first startedwriting the Missing Semester, I
was writing like every financebook.
I was writing everything I hadlearned at Carnegie Mellon
through, you know, getting theCFA designation, expounding all
this finance information thatpeople had to hear, and I
remember I was 15 pages intochapter one.

(07:44):
I thought wait a minute.
Is anyone still reading?

Steve Davenport (07:48):
Yeah, I mean, did you solve the pricing of the
options?

Gene Natali (07:53):
No, I shredded it.
I said this has been done.
There's a lot of thick booksout there espousing what the
finance industry knows.
There's not a short actionablebook.
Missing semester is a money 101actionable book excuse me,
actionable book.
The missing second semester isinvesting 101.
Trout would take that samephilosophy because, after giving

(08:14):
my thousandth presentation onthe missing semester on personal
finance and giving a room fullof fist bumps, I said geez, fist
bumps aren't enough.
You could 10X these fist bumps,but there has to be fist bumps
aren't enough.
You could 10x these fist bumps,but there has to be an action
step if we're going to move theneedle.
And it's not enough to keepsending speakers in rooms.
We need to lift up and empoweran industry if we actually want

(08:36):
to move the needle.
And, steve, the pinnacle ofthis was 2019, a meeting at the
United Nations headquarterswhere a couple of the board
members said don't stop whatyou're doing.
The world needs good softwarein this space.
So Troutwood took the samemissing semester philosophy of
simple, easy, actionable.

Steve Davenport (08:57):
No, I agree.
We tried to do something withvideos because we felt there was
honest advice about what peopleshould do, without an incentive
from the financial firm whosponsored the videos.
We wanted it to be non-biasedand we tell some hard truths

(09:21):
about people doing theirbudgeting and you know why.
Spending is a dangerous animalto try to control.
And you've got the world ofretailers who want you to pass

(09:43):
that phone over the checkoutline and they want you to just
hit that big blue button becauseit makes people feel good when
they click on and they buysomething.
And you, you we're trying to,you know, preach to people or to
educate people in a way thatothers haven't, and it's not
because you know, they justdidn't feel like it.
It's difficult and it'sdifficult to get people to say
don't consume today, delaygratification for some tomorrow.

(10:05):
Just those two words delaygratification.
This is 2025.
We have attention spans ofseven to eight seconds.
You know what I mean.
This isn't 1975, where you hadone minute attention spans.
You had one minute attentionspans.
You've got to really thinkabout how your messaging can

(10:26):
affect the most people andaffect the most lives.
And I agree, you are taking thenext step from some education.
Okay, now how do I implementthe solution in a way that's
going to set up my 401k account.
Look at the areas I can live.
And I think you still have thatpart of your application where
you said, hey, if I got a jobhere or here, let me compare

(10:48):
what the budget would be for thetwo locations.
That was great thinking, becausecollege students guess what I
mean.
They're not you know.
I mean I've, I've been in frontof those hundred college
students and got those fistbumps.
But I sit there and I say thisis a college of you know at
Georgia, with 34,000 students,and I've got a hundred of them

(11:29):
You're pursuing.
Technology was I think you knowwhat I mean a way to quickly
transmit those ideas and thosedisciplines and those questions
to people so that they couldsucceed.
And I guess I ask is, in theworld of AI, where does trouble
end up?

Gene Natali (11:38):
Yeah, quietly doing some great work.
So we built secure AI.
Our individual users have AIthat reads their individual
financial plan.
Our enterprise and financialadvisor partners have AI that
sits over their participantemployee, customer cohort base.
It's secure, which means weboxed it in on top of the open

(11:59):
AI platform.
I think that's extremelyimportant.
Finance industry trust isnon-negotiable, which means you
should be using secure AI.

Steve Davenport (12:17):
Yeah, I mean I don't want to divert too much
know, troubled by what I seewith companies and banks and it
feels like banks could easilyturn into utilities the way that
they're doing things.

Gene Natali (12:33):
And I'll put an aggressive comment on top of
that Banks and financialadvisors have a generational
opportunity to own their futureif they act.
They have the opportunity to bethe center of an individual, of
a small business's financiallife, if they choose to act.
And the opportunity theconsumer and the small business

(12:53):
are begging for it.
I hope that the industry hears,sees and acts.
Our platform was built toempower it.
The industry hears, sees andacts.
Our platform was built toempower it.
So I say that very selfishlyand very biasly as someone who
believes it, but I'm seeing itfrom both sides of the barbell.

Steve Davenport (13:08):
Well, I just look at, you know, the average
individual and how are they ableto, you know, make, get past
inflation and understandinflation and what?
What does it impact and howdoes it impact and how can I
immunize myself somewhat from it?
Should I be buyinginflation-linked bonds instead
of treasuries or corporate bonds?

(13:29):
I think there's a lot of workthat we as an industry of
investment professionals butjust finance professionals I
think there's plenty of room inthis.
You know, uh, in this boat, andI want to get in the boat and
and start, you know, paddling,because I think that we, you

(13:50):
know, we've got a long journeyahead of us.
So I guess, how, how do you seewhat?
Can you just give me abeginning to end of how you
would like someone's financialeducation and implementation to
go?
So a student comes to you andsays, hey, I want to do a
financial plan.
We give them Troutwood, they dothe financial plan.

(14:14):
Then the financial planundergoes some rigor in terms of
where do you work and how muchdo you make and how, what is
your savings amount and how muchdo you want to spend?
And, um, I, I guess, is there.
Um, do you still think the 50,30, 20 kind of model works, or

(14:34):
do you think we're, as a society?
You, uh, is life becoming morelike 60?
Um, you know, and and the, theuh, the savings is going to 10.
Um, because that's what itfeels like when I talk to my
kids and and people around methat life is more expensive and

(14:56):
I don't know where you get that50%, dad.
But it's you know and the, theplace that I don't want to give
up is my, you know, want.
The place that I unfortunatelygive to see people giving up is
their savings.
I mean, how does the model oftoday, just like asset
allocation needs to includealternatives Does?

(15:19):
Does something else need to bein there for inflation?

Gene Natali (15:25):
So I'll answer both questions.
The first was the student whoapproaches Troutwood.
On Troutwood, we have threeproducts.
We have Troutwood Basic, whichis a career exploration, cost of
living modeling, investmentmodeling that gives an
individual their first workingfinancial plan from a data set
of about 115 million unique datapoints.

(15:45):
The reason that matters and oneof our strongest KPIs at
Troutwood is nearly 100% of ourstudent users complete their
plan.
That's a massive data point.
What that means is they're nowentering the real world informed
.
What they do with theinformation, as has been true in
all of history, is up to theindividual, but we can at least

(16:07):
help graduate a more informedstudent.
Our two follow-on products areTroutwood Pro.
Troutwood Pro is our living,breathing financial plan that
helps guide an individual totheir retirement or financial
goal in partnership with afinancial advisor, bank,
employer Any of those threesilos we need support.

(16:31):
Right now.
We push individuals out on alifeboat and say good luck with
your financial life.
We're building a world wherethey'll have the support of all
three of those partners.
The third and final product isour engagement and incentive
platform that is administered bythe advisor, the bank or the
employer to help that individualunderstand where they're going

(16:52):
and why.
You know that's the journeythat we build.
So it is an end to end fullplatform from as young and Steve
.
Some of our strongest users areearly teens, where they have a
paycheck and a Roth IRA and theylove having their financial
life in one place.
So less and more bank orfinancial advisor partners are
hearing that and beginning toact.
The other question you askedthe 50-30-20,.

Steve Davenport (17:28):
It depends on when that individual chooses to
start.
The earlier they start, rightthe different numbers are,
versus the later they start.
Gosh, if you wait till reallyold, it's 100% safe.
Financial literacy start andhow do we do it such that it
becomes ingrained in theirpersonality?
And you know we were reading tosecond and third graders
because if you can help peoplewith that delay in gratification
, they become better.

(17:49):
Ultimately, financial literacycandidates and I still believe
that you know it's up tofamilies and I believe it's up
to educational institutions andchurch and other places to
supplement what is your messageto people?
Because guess what, if thestudents become better with

(18:12):
their money, I think thebeneficiary is going to be the
university they say, hey, theytaught me and the community and
the employers.
It helps the stability of theemployees, it helps the lifespan
, it helps them, you know, haveless stress and be healthier.
There's tons of benefits andyou and I don't think could

(18:34):
spend 30 minutes on benefitsalone and the conversation would
be incomplete.
I really would love to get fromyou is where do you see the
hotspots of areas that are verydifficult to solve and where do
you see success really coming tofruition such that we should,

(18:56):
you know, we should promotethose people who are pushing
success and we should, you know,encourage and support those
people who are trying to dealwith the most difficult
situations.
I had a group in Orlando thatwas going after people in
homeless shelters and trying tohelp them with everything to get
their life back in order,including financial literacy

(19:17):
everything to get their lifeback in order, including
financial literacy.
And my point of view was boy,that's taking on a big piece of
the pie, right, and I guessyou're cutting this pie every
day trying to figure out what dowe do for middle age?
What do we do for startingcareer?
What do we do Like?
Where are we really getting itright and where are we still

(19:37):
having challenges?

Gene Natali (19:40):
It's a giant question, Steve, and I will
answer it.

Steve Davenport (19:45):
Well, you're a giant of this industry.

Gene Natali (19:49):
I've been working tirelessly at solving that for
15 years and I'll preface myanswer.
We've got a client inBrownsville, texas.
They're a very poor, poorregion of Texas.
It's called Troutwood a giftfrom God.
We work with VirginiaCommonwealth University, their
financial wellness center onefinancial wellness center of the
year last year Virginia'sCommonwealth Savers program has

(20:09):
taken the unique step ofempowering their employees with
Troutwood platforms.
So you're seeing folks start totiptoe and the reason I am
saying that, the analogy thatyou give in the loaded question
what if the pieces that yousuggested were parts of the
equation and not the wholeequation?
The community, the church,right, the employer?

(20:31):
What if the financial industryled like the dental industry?
What Brush your teeth?
Every parent is saying brushyour teeth before bed.
What if every parent was sayingdid you save and invest $3
today?
Because the financial industrytook time to understand?

(20:52):
Wait a minute.
We have a $14 trillionshortfall because of our past
mistakes.
What if we solve it startingnow?
And that's $14 trillionshortfall because of our past
mistakes.
What if we solve it startingnow?
And that's $14 trillion ofassets moving forward If we
started to play offense?
Personal opinion way too muchfinancial literacy education has
been token, I was there, gave apresentation.

(21:13):
Check the box.
No, no, no, no.
The audiences that youmentioned not everyone grew up
with a Wall Street Journal onthe dining room table.
Right you walk into.
This time there's going to bekids doom scrolling on TikTok.
We need to look them in the eyeand say you can do this.
We need to bring analogies likebrushing your teeth that they
can relate to and they have totouch and feel it.

(21:36):
We have a fourth product Ididn't talk about but we're very
proud of.
It's a map of the stock marketStudent users.
Over an hour and a half in ourmap each month on average.
Why?
It's no different than cheeringfor your high school football
team or the Patriots or theSteelers.
They are proud of the companiesin their communities because
they know people that work there.

(21:57):
Proud of the companies in theircommunities because they know
people that work there.
The future of investing isn'tPE ratio versus Sharpe ratio if
we want to include thenon-investors.
It's understanding that my mom,my dad, my aunt, my neighbor
works at Dick's Sporting Goodsand connecting the dot that when
they walk in they can own ashare of Dick's Sporting Goods.
They can be a part of thissystem.

(22:21):
So I think it has to start atthe top, steve.
The industry has got to stepinto a leadership role Banks,
financial advisors, technologywill be a part, because
technology creates the scalethat makes possible what we're
talking about.

Steve Davenport (22:35):
Yeah, well, I have an advisory board for our
firm, Circa Capital, and on thatboard is a young RIA and his
idea that we're trying to workour way out of is to come up
with a portfolio for the peoplein North Carolina, South
Carolina and Georgia ofcompanies that are in our
community that we feel like ifpeople own the companies that

(23:00):
they see around them and work on, they would feel much better
about their investments becausethey know when they go to Bodex
or they know when they go to youknow online to get a Microsoft
package, they'd say, hey, I ownsome shares of of this.
And I think that the investmentindustry customizing for people

(23:22):
and saying you live in thisstate, here's a, here's a you
know the top 20 employers are,you know these companies and
they're in your portfolio andand that to is one way as an
industry, we can get people tobehave better Because ultimately
, we can give people education,we can give people tools that

(23:46):
they can implement, but it's thethat behavior.
As an individual at 19, 20, 21,you would love to see good
discipline and things occur, butyou know what?
It's pretty damn hard to get ajob.

(24:07):
So I can understand why peopleare job first.
You know financial literacylater.
I think you might pick a betterjob and have better
determination of results if yougot the financial literacy later
.
I think you might pick a betterjob and have better
determination of results if yougot the financial literacy as
you were looking for the job andyou incorporated those factors
in your decision making.
But I think that you know.

(24:30):
One of the questions I have ishow are we distributing
Troutwood and how easy is it?
For if we include Troutwoodcomon our podcast, what will be the
result?
Or what can I do for people whoare listening to help them with

(24:52):
Troutwood as an advocate and asa tool?

Gene Natali (25:00):
advocate and as a tool.
Thank you for that question,steve.
For the podcast link, link ourmap of the stock markets because
it's an actionable fund tool inour basic application, which is
free and it's out there foranyone to build their financial
plan.
We don't have our pro productor enterprise product on our
website, but individuals can DMme directly.
I can give you my email address, all of my social contacts, et
cetera, and that's intentional.

(25:22):
That will change Our website is.
We're building as a softwarecompany should and could the Buy
Now button where any financialadvisor, any financial
institution, any employer of anysize will be able to hop on,
buy their licenses and getrunning.

Steve Davenport (25:36):
Yeah, I mean, are you keeping track of some of
these stories?
I mean I'd love to read aboutthis Virginia Commonwealth and
the Brownsville Texas person andthe cause to me, those, those
inspire me.
To you know, we can.
We can create a, a, a what I'llcall a center of excellence in
different.
You know, here's an RIA who isa center of excellence here.

(25:57):
You know, here's an ria who's acenter of excellent.
Here's a school that's a centerof excellent.
Here's a church that's a centerof excellent.
Because to me, I think peopleare looking for a solution here
and I think that the world,because of our lack of attention
span and our complexity of allthe problems that are being
dealt with daily, it's hard toget to cut through the fog and

(26:21):
get to where we really can helppeople.

Gene Natali (26:24):
I love that, steve.
I believe so strongly what yousaid.
I started a business.
That's a problem, right?
The world is looking forinspiration, it's demanding it
and I remain stunned that thethree we keep saying this broad
industry.
But why are employers notresponding?

(26:46):
Get back those 20 days ofproductivity.
It costs a few bucks toimplement a Troutwood-like
financial wellness tool.
The ROI on that is stunning.
What are they doing that?
Historically, we've just putjust good enough tools to check
the box.
Good enough tools to check thebox.

(27:07):
I want to speak really quicklyto your CFA and CFP audiences
because you hit on somethingvery important with that
community touch that you talkedabout three minutes ago.
We live in an industry that isfocused on alpha outperformance
finding the right stocks.
What the finance industry hasmissed for years is the delta.
The difference between doingnothing is far greater than the

(27:33):
alpha from the right or wrongstock pick.
Have to involve people in thissystem.
It's inspiration, but it'sinspiration that drives action
and makes them feel confidentthat this is a story I want to
be a part of.
I trust my money that I workhard for in this system.

(27:54):
That, in my opinion, is a big,big area where we are failing is
ignoring the delta, thedifference of doing nothing
nothing.

Steve Davenport (28:07):
Yeah, I mean, I've always tried to look at the
communities and say, okay, youknow, there's 35% of the
population that I would say ischallenged or, you know, fragile
.
And then I would say there'sanother 30% that is trying to
rise up and in that stagethey've got a lot of challenges,
they need a lot of tools, butthey they do have jobs and they
do have personal lives that theycould potentially get.

(28:29):
And then there's what I'll callthe college educated rest, and
that college educated rest theyhave a lot of advantages and
they're going to have a lot ofsuccess.
But there's a lot of people inthere that still don't do things
you know, very logically orvery helpful to their financial
help with food and supportmechanisms, donate to groups for

(29:09):
the middle that help witheducation and donate to groups
that are kind of reaching outand using social media to go
after that top 30.
I don't know how we make adifference, but we've got one
minute to figure out how.

Gene Natali (29:31):
Give a hand up, not a handout right.
Where people choose to donatetheir money should always be
personal and it's an importantimpact tool.
But no different than thatanalogy I gave on looking at
past and saying we're $14trillion short.
How do we make that a $14trillion offensive move for the
industry moving forward?
It's no different.

(29:54):
If we empower a generation toact, it will massively move the
needle and outweigh anycharitable impact.
So donate your money in theareas that are important to you
as a human being and teachpeople how to build better lives
.
Create an action step.

Steve Davenport (30:06):
That's great, gene.
That's a great point for us toend on.
I mean, I think you know all ofour listeners I'm going to, you
know, cover this podcast with alot of ways to contact and
reach out and see if some ofGene's could work.
But I really want everyone totry to think about is there
someone you could help?
Is there someone you know who'shaving financial questions and

(30:27):
challenges?
Help them, share thisinformation about this tool and
you know, if everybody whoreaches out to two or three
people, we can start to make areal difference.
So, gene, thank you very muchfor being here today and I'd
love to come.
You come back when you know wehave another moment in the sun

(30:47):
for financial literacy and yourfirm.
I'm supporting you, I believein you and I hope all my
listeners will too.
So thanks for being here today.

Gene Natali (30:58):
Steve likewise, thank you so much, and thank you
to everyone listening.
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