July 5, 2025 • 16 mins
Caroline Biesalski introduces Freddie Rappina, who shares insights on learning from mistakes in financial management. The discussion explores the analogy of checkers versus chess in finance, emphasizing strategic thinking and the benefits of using loans to acquire assets. They address common financial pitfalls and the importance of shifting perspectives on taxes, as well as navigating the challenges of starting with limited resources. Freddie highlights the role of mentors, learning from mistakes, and sources of inspiration in his journey. He also discusses his book and upcoming projects. The episode wraps up with final thoughts on success and financial strategy, along with a special offer for listeners.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
So you don't make the same mistake on a largething, because then those, you know, if you
make a mistake on something that's, you know,make a 10% mistake on, you know, a $1,000
thing, it's $100, right?
If you make, you know, a 10% mistake on a$1,000,000 thing, that's $100,000.
So it's making sure that you'll learn you'rewading into the water a little bit.
(00:23):
So when those mistakes do happen, and theywill, it doesn't it doesn't it's just a bad
day, and you're like, oh, shucks.
I'm just not gonna do that again, and you learnfrom it.
But it doesn't it doesn't take you out.
Welcome to Inspired Choice Today.
I'm your host, Caroline Biesalski, here tobring you authentic stories, surprising
lessons, and powerful takeaways to fuel yourjourney in business and life.
(00:48):
In each episode, I'll take you from oneinspiring guest to the next, blending their
experiences with my expertise to uncoverpractical strategies you can use right away.
Whether you're starting out or stepping up,stay tuned for insights and actionable tips
that make a difference.
And stick around until the end for a specialfreebie just for our listeners.
(01:15):
Hello, and welcome, Inspired podcast community.
I have to smile already.
This is your new episode.
My name is Caroline, and my today's guest isFreddie Rappina, and I hope I pronounced your
name right.
You taught me how to do this.
How are you doing today?
I'm doing great, and you can answer just fine.
(01:36):
Thank you so much.
I'm always willing to learn, and I would liketo introduce you to the audience, of course.
Oh my goodness.
Where are you?
So I have I have here a short bio of yours.
Most people play checkers with their finances,saving for security.
The wealthy play chess, leveraging assets forcash flow and growth.
(01:57):
The difference?
It's not luck.
It's strategy.
Ready to level up your financial game?
Then listen to this podcast.
And I can tell you something.
It is so funny because I told this in theepisode before because I recorded it the same
day, so to say.
And I generate my the bio and the questions byAI.
(02:20):
Right?
And I used the wrong prompt today.
So I have something like a it's, like amarketing it's like an advertisement or
something.
It's not questions, but I corrected it alreadyfor you.
So the bio is a little bit but it is you.
Right?
It is you?
That is me.
Yes.
And I have questions.
(02:41):
Of course, this is the most important thing.
You say most people play checkers with theirfinances while the wealthy play chess.
What's the first strategic move someone shouldmake to switch from saving for security to
building cash flow and growth?
Okay.
That's a real good question.
And, first of all, let me say there's nothingwrong with playing checkers.
(03:05):
And if you're gonna play checkers, I want youto play it very well.
You know, save diligently in retirementaccounts, have no debt, you know, invest for
the future, college plans, all that stuff.
Right?
But if you're interested in playing chess, toanswer your question, I think the biggest thing
(03:26):
that you have to set you have to change in yourmindset is your attitude towards debt, towards
leverage.
So if you're playing checkers, like I justsaid, you wanna be out of debt.
If you're playing chess, you actually wanna bein as much debt as possible.
And when I'm using debt in this context, I'mnot talking about running your credit card up.
(03:49):
I'm talking about using loans to purchaseassets that produce cash flow, which a portion
of that cash flow pays back the loan and aportion of that cash flow goes into your
pocket.
So you can enjoy your life now, not waiting 30years for compound interest or any other
(04:10):
strategies that are kind of pushed in thecheckers mindset.
Wow.
I understand what you mean.
So not waiting until retirement and then toplay chess means to use the loan twice to
invest in assets.
And I heard this before, not in liabilities.
There's a difference.
And I studied.
(04:31):
Yeah.
You Well, you definitely don't wanna use theloans for liabilities.
You use loans for the assets.
Now you can cover a liability with an assetwith a loan.
A good example of that is like cars.
Right?
So instead of just purchasing or just financinga car, you could first use a down payment to,
(04:55):
and take out a loan to purchase a rentalproperty.
And that rental property produces cash flow.
The excess cash flow can be used to pay for acar loan.
So the asset is paying both loans, not out ofyour pocket.
And at the end of the loan term for thevehicle, you have all your money.
(05:17):
It's still sitting in the asset.
Yes.
You have all the money and the car on top.
Yes.
Right.
And the car.
Wow.
These are valuable strategies.
Thank you so much for sharing.
And, of course, I have another question.
It is k.
What's a common financial habit that keepspeople stuck in the middle-class mindset, and
(05:39):
how can they break free from it to startthinking like the wealthy?
In addition to using debt properly and havingthat attitude, their attitude towards taxes
also should probably change because the taxcode, especially in the U.S., is a guide to not
(06:01):
pay taxes, which people have a hard timewrapping their heads around, even that
statement.
It's a guidebook.
They're telling you through the tax code, ifyou do these things, you don't have to pay as
much in taxes.
But it's a free country, free will.
If you don't do these things that I'm askingyou to do, that's fine.
(06:25):
But I have to take more taxes from you becauseI need to still, you know, pay for roads,
bridges, and defense funds and everything else.
So I think that once people change theirmindset towards taxes as well and start using
it to their advantage, not to their detrimentand not just throwing their hands up in the
(06:47):
air, thinking that no matter what they do, it'salways gonna be, you know, you're gonna get
taxed very heavily.
I think that's a mistake.
Yes.
I understand.
So it's a free country, and you always have thechoice to pay really high taxes or I don't know
how you call this.
(07:07):
It's your choice.
Or you use the tax code, as you said, to pay as
Or
Yes.
You're paying, and the reason why you're payingless in taxes is because what you're doing is
benefiting the government in some form orfashion.
Every tax break in the tax code is meant toincentivize people to do something because that
(07:33):
something benefits the government.
So it's a win-win when you start accepting thetax code as an ally and, you know, whether
you're starting a business, which creates jobs.
Right?
And that's the government likes that.
You're creating more of a tax base, you know,purchasing real estate.
(07:53):
You get depreciation on the real estate becausethe government wants you to have lots of people
to invest in housing this way.
It keeps the rent low or as low as, you know,market rate because there's a lot of landlords
competing for renters, which in theory shouldkeep the rent low.
(08:14):
I know some people may have a different opinionon that one.
Even just having kids.
Right?
You know, the government gives you tax breaksfor having kids.
And that's because they're incentivizing tocreate future taxpayers.
So, you know, those kids are gonna grow up andbe, and be more of a tax base.
So if you start looking at it like that, youknow, it does change your mindset a little bit.
(08:38):
Wow.
I love what you said.
You said something like the tax code is yourbest friend when you use it wisely.
Yeah.
I think you gotta think of it like a big couponbook or, you know, something that, you know,
relates to you.
Like, something that makes life easier for you,and it's a win-win.
(08:58):
Like I said, it's a win-win situation for thegovernment.
Oh, thank you so much for sharing.
I'm highly inspired now.
Of course, I have another question.
If someone is starting with limited resources,what's the quickest way they can begin
leveraging their assets to create long-termfinancial growth?
It's a good question.
(09:19):
You may have to play checkers first.
Right?
And you may have to have a good checkers gamegoing before you can switch over to that chess
mindset because that's when you're buildingthat access.
You're building that capital.
The trick is to just not use it.
Right?
(09:39):
Once you have it, and if you want to switchover to chess, don't use the money.
Don't pay cash for something when you can takeout a loan to buy the asset with the loan.
Right?
So it's that mindset, but the trick is you haveto have a good amount of money to make the risk
low.
When people start just overleveraging, like abad chess move is when they all start
(10:03):
overleveraging, and they get the cart in frontof the horse a little bit, and that can turn
into a house of cards real fast.
You don't want to do that.
You actually want to have the assets, andhaving those assets is what makes the lenders
want to give you the loan.
So because they believe that you are a goodbet, that you're going to pay them back.
So, you know, if people have limited resources,they should probably start with a real good
(10:28):
checkers game first.
Okay.
I understand.
This is good advice.
I appreciate that so much.
Thank you so much.
And also your analogies about the gaming world.
Mhmm.
The house of cards, for example.
Mhmm.
Okay.
Card play or play of cards or something.
Yes.
(10:48):
Thank you.
Yeah.
I mean, if we see it a lot when people start,even when they start moving over to just and
they start, yeah, like, they get just so easy.
Like, it's not easy.
Right?
And they start taking out loans they shouldn't.
They start overleveraging, you know, somethinghappens, and it all comes crashing down.
So but being you wanna invest from a positionof strength.
(11:11):
So it's just a different way of looking at it.
That's so true, and that reminds me of what Ionce did.
It was but we learn from our failures or ourmistakes as well, or we have someone like you
guiding us.
And my question is because you help people tonot make mistakes.
(11:34):
And, do you have coaches or mentors foryourself?
And who was the best coach you ever had?
I don't know.
Well, the best coach I ever had was a mentor ofmine.
He was a real estate broker.
And, you know, just he was very brash and very,like, in your face, and he you know, just you
(11:58):
you can do this.
Right?
This if you choose to, you know, start buildingwealth, you can do it.
And, you know, it was very refreshing to hearsomeone say that.
Right?
And, you know, making mistakes is okay.
If you're not making mistakes, you're not doingenough.
But those mistakes should be on small things.
(12:22):
So you don't make the same mistake on a largething because then those, you know, if you make
a mistake on something that's, you know, make a10% mistake on, you know, a $1,000 thing, it's
$100, right?
If you make, you know, a 10% mistake on a $1million thing, that's $100,000.
So it's making sure that you'll learn you'rewading into the water a little bit.
(12:45):
So when those mistakes do happen, and theywill, it doesn't it doesn't it's just a bad
day, and you're like, oh, shucks.
And just not gonna do that again, and you learnfrom it.
But it doesn't it doesn't take you out.
Yes.
That's so true.
Thank you for reminding us, and I would like toknow where we can find you when people want to
reach out to you after listening to thisepisode.
(13:09):
You can go to optifinancial.com.
That's our firm.
It's a boutique wealth management firm.
And also, you can find my book on Amazon orBarnes & Noble, wherever.
It's called Playing the Wealth Game.
Good information in this about learning themindset between checkers and chess and, you
(13:34):
know, complimentary consultations on ourwebsite.
People can just, you know, reach out to us andlet us try to help you.
And if we can, we can.
If it's a good fit, it's a good fit.
If it's not, you know, no harm, no foul.
I love it.
Thank you so much.
Please reach out to Freddie.
He's amazing.
He shares his wisdom about wealth, and I lovebooks as well.
(13:57):
I will check it.
This is the word.
I will check it first and then play chess, ofcourse.
Thank you so much.
I have one last question.
It is about your goals and intentions.
Do you set goals for yourself, and what is oneof your next projects?
My, my next projects are, buying an apartmentbuying apartment buildings.
(14:22):
But, I would say my goal for myself is just tocontinue helping my clients, continue building
a good client base, you know, especially peoplethat wanna play chess, people who, you know,
it's it's nice when you hear hear from yourclients how communicative you are, you answer
the phone, and that type that, you know, thattype of stuff.
(14:43):
And, you know, just continue building thisthis, you know, my firm to, to a great
reputable status in the marketplace.
Wow.
I love it.
Thank you so much for sharing.
Now it's time for your final thoughts to theaudience, please.
Well, I would say that successful people arethe people willing to do the things that they
(15:05):
don't want to do in order to get where you wantto be.
If you're, you know, one of the goals of thebook was to help people stop screaming at the
moon.
Why do the rich keep getting richer and othersnot?
It's because you're playing a different game.
And, you know, there's definitely a do as Isay, not as I do element in the financial
(15:25):
world.
So we need to be on the lookout for that.
And just don't, you know, follow what peopleare doing, not just what they're saying,
because there's a lot of people out there thatare getting very wealthy from teaching checkers
and then playing chess.
So, you know, just find a guide that's going tobe right for you.
(15:50):
I love this message.
Thank you so much.
This was a great interview.
Thank you.
Thanks for having me.
And see you in the next episode.
Thank you for listening to Inspired ChoiceToday.
I'm thrilled to have you on this journey ofgrowth and transformation.
Don't forget to hit follow or subscribe to stayconnected and never miss an episode.
(16:15):
And here's something special.
Grab your free 20-minute breakthrough sessionwith me.
It's designed to help you kick-start or levelup your business.
Just check out the show notes for more.
Until next time, keep making those inspiredchoices and see you in the next episode.
So you don't make the same mistake on a largething, because then those, you know, if you
make a mistake on something that's, you know,make a 10% mistake on, you know, a $1,000
thing, it's $100, right?
If you make, you know, a 10% mistake on a$1,000,000 thing, that's $100,000.
So it's making sure that you'll learn you'rewading into the water a little bit.
(00:23):
So when those mistakes do happen, and theywill, it doesn't it doesn't it's just a bad
day, and you're like, oh, shucks.
I'm just not gonna do that again, and you learnfrom it.
But it doesn't it doesn't take you out.
Welcome to Inspired Choice Today.
I'm your host, Caroline Biesalski, here tobring you authentic stories, surprising
lessons, and powerful takeaways to fuel yourjourney in business and life.
(00:48):
In each episode, I'll take you from oneinspiring guest to the next, blending their
experiences with my expertise to uncoverpractical strategies you can use right away.
Whether you're starting out or stepping up,stay tuned for insights and actionable tips
that make a difference.
And stick around until the end for a specialfreebie just for our listeners.
(01:15):
Hello, and welcome, Inspired podcast community.
I have to smile already.
This is your new episode.
My name is Caroline, and my today's guest isFreddie Rappina, and I hope I pronounced your
name right.
You taught me how to do this.
How are you doing today?
I'm doing great, and you can answer just fine.
(01:36):
Thank you so much.
I'm always willing to learn, and I would liketo introduce you to the audience, of course.
Oh my goodness.
Where are you?
So I have I have here a short bio of yours.
Most people play checkers with their finances,saving for security.
The wealthy play chess, leveraging assets forcash flow and growth.
(01:57):
The difference?
It's not luck.
It's strategy.
Ready to level up your financial game?
Then listen to this podcast.
And I can tell you something.
It is so funny because I told this in theepisode before because I recorded it the same
day, so to say.
And I generate my the bio and the questions byAI.
(02:20):
Right?
And I used the wrong prompt today.
So I have something like a it's, like amarketing it's like an advertisement or
something.
It's not questions, but I corrected it alreadyfor you.
So the bio is a little bit but it is you.
Right?
It is you?
That is me.
Yes.
And I have questions.
(02:41):
Of course, this is the most important thing.
You say most people play checkers with theirfinances while the wealthy play chess.
What's the first strategic move someone shouldmake to switch from saving for security to
building cash flow and growth?
Okay.
That's a real good question.
And, first of all, let me say there's nothingwrong with playing checkers.
(03:05):
And if you're gonna play checkers, I want youto play it very well.
You know, save diligently in retirementaccounts, have no debt, you know, invest for
the future, college plans, all that stuff.
Right?
But if you're interested in playing chess, toanswer your question, I think the biggest thing
(03:26):
that you have to set you have to change in yourmindset is your attitude towards debt, towards
leverage.
So if you're playing checkers, like I justsaid, you wanna be out of debt.
If you're playing chess, you actually wanna bein as much debt as possible.
And when I'm using debt in this context, I'mnot talking about running your credit card up.
(03:49):
I'm talking about using loans to purchaseassets that produce cash flow, which a portion
of that cash flow pays back the loan and aportion of that cash flow goes into your
pocket.
So you can enjoy your life now, not waiting 30years for compound interest or any other
(04:10):
strategies that are kind of pushed in thecheckers mindset.
Wow.
I understand what you mean.
So not waiting until retirement and then toplay chess means to use the loan twice to
invest in assets.
And I heard this before, not in liabilities.
There's a difference.
And I studied.
(04:31):
Yeah.
You Well, you definitely don't wanna use theloans for liabilities.
You use loans for the assets.
Now you can cover a liability with an assetwith a loan.
A good example of that is like cars.
Right?
So instead of just purchasing or just financinga car, you could first use a down payment to,
(04:55):
and take out a loan to purchase a rentalproperty.
And that rental property produces cash flow.
The excess cash flow can be used to pay for acar loan.
So the asset is paying both loans, not out ofyour pocket.
And at the end of the loan term for thevehicle, you have all your money.
(05:17):
It's still sitting in the asset.
Yes.
You have all the money and the car on top.
Yes.
Right.
And the car.
Wow.
These are valuable strategies.
Thank you so much for sharing.
And, of course, I have another question.
It is k.
What's a common financial habit that keepspeople stuck in the middle-class mindset, and
(05:39):
how can they break free from it to startthinking like the wealthy?
In addition to using debt properly and havingthat attitude, their attitude towards taxes
also should probably change because the taxcode, especially in the U.S., is a guide to not
(06:01):
pay taxes, which people have a hard timewrapping their heads around, even that
statement.
It's a guidebook.
They're telling you through the tax code, ifyou do these things, you don't have to pay as
much in taxes.
But it's a free country, free will.
If you don't do these things that I'm askingyou to do, that's fine.
(06:25):
But I have to take more taxes from you becauseI need to still, you know, pay for roads,
bridges, and defense funds and everything else.
So I think that once people change theirmindset towards taxes as well and start using
it to their advantage, not to their detrimentand not just throwing their hands up in the
(06:47):
air, thinking that no matter what they do, it'salways gonna be, you know, you're gonna get
taxed very heavily.
I think that's a mistake.
Yes.
I understand.
So it's a free country, and you always have thechoice to pay really high taxes or I don't know
how you call this.
(07:07):
It's your choice.
Or you use the tax code, as you said, to pay as
Or
Yes.
You're paying, and the reason why you're payingless in taxes is because what you're doing is
benefiting the government in some form orfashion.
Every tax break in the tax code is meant toincentivize people to do something because that
(07:33):
something benefits the government.
So it's a win-win when you start accepting thetax code as an ally and, you know, whether
you're starting a business, which creates jobs.
Right?
And that's the government likes that.
You're creating more of a tax base, you know,purchasing real estate.
(07:53):
You get depreciation on the real estate becausethe government wants you to have lots of people
to invest in housing this way.
It keeps the rent low or as low as, you know,market rate because there's a lot of landlords
competing for renters, which in theory shouldkeep the rent low.
(08:14):
I know some people may have a different opinionon that one.
Even just having kids.
Right?
You know, the government gives you tax breaksfor having kids.
And that's because they're incentivizing tocreate future taxpayers.
So, you know, those kids are gonna grow up andbe, and be more of a tax base.
So if you start looking at it like that, youknow, it does change your mindset a little bit.
(08:38):
Wow.
I love what you said.
You said something like the tax code is yourbest friend when you use it wisely.
Yeah.
I think you gotta think of it like a big couponbook or, you know, something that, you know,
relates to you.
Like, something that makes life easier for you,and it's a win-win.
(08:58):
Like I said, it's a win-win situation for thegovernment.
Oh, thank you so much for sharing.
I'm highly inspired now.
Of course, I have another question.
If someone is starting with limited resources,what's the quickest way they can begin
leveraging their assets to create long-termfinancial growth?
It's a good question.
(09:19):
You may have to play checkers first.
Right?
And you may have to have a good checkers gamegoing before you can switch over to that chess
mindset because that's when you're buildingthat access.
You're building that capital.
The trick is to just not use it.
Right?
(09:39):
Once you have it, and if you want to switchover to chess, don't use the money.
Don't pay cash for something when you can takeout a loan to buy the asset with the loan.
Right?
So it's that mindset, but the trick is you haveto have a good amount of money to make the risk
low.
When people start just overleveraging, like abad chess move is when they all start
(10:03):
overleveraging, and they get the cart in frontof the horse a little bit, and that can turn
into a house of cards real fast.
You don't want to do that.
You actually want to have the assets, andhaving those assets is what makes the lenders
want to give you the loan.
So because they believe that you are a goodbet, that you're going to pay them back.
So, you know, if people have limited resources,they should probably start with a real good
(10:28):
checkers game first.
Okay.
I understand.
This is good advice.
I appreciate that so much.
Thank you so much.
And also your analogies about the gaming world.
Mhmm.
The house of cards, for example.
Mhmm.
Okay.
Card play or play of cards or something.
Yes.
(10:48):
Thank you.
Yeah.
I mean, if we see it a lot when people start,even when they start moving over to just and
they start, yeah, like, they get just so easy.
Like, it's not easy.
Right?
And they start taking out loans they shouldn't.
They start overleveraging, you know, somethinghappens, and it all comes crashing down.
So but being you wanna invest from a positionof strength.
(11:11):
So it's just a different way of looking at it.
That's so true, and that reminds me of what Ionce did.
It was but we learn from our failures or ourmistakes as well, or we have someone like you
guiding us.
And my question is because you help people tonot make mistakes.
(11:34):
And, do you have coaches or mentors foryourself?
And who was the best coach you ever had?
I don't know.
Well, the best coach I ever had was a mentor ofmine.
He was a real estate broker.
And, you know, just he was very brash and very,like, in your face, and he you know, just you
(11:58):
you can do this.
Right?
This if you choose to, you know, start buildingwealth, you can do it.
And, you know, it was very refreshing to hearsomeone say that.
Right?
And, you know, making mistakes is okay.
If you're not making mistakes, you're not doingenough.
But those mistakes should be on small things.
(12:22):
So you don't make the same mistake on a largething because then those, you know, if you make
a mistake on something that's, you know, make a10% mistake on, you know, a $1,000 thing, it's
$100, right?
If you make, you know, a 10% mistake on a $1million thing, that's $100,000.
So it's making sure that you'll learn you'rewading into the water a little bit.
(12:45):
So when those mistakes do happen, and theywill, it doesn't it doesn't it's just a bad
day, and you're like, oh, shucks.
And just not gonna do that again, and you learnfrom it.
But it doesn't it doesn't take you out.
Yes.
That's so true.
Thank you for reminding us, and I would like toknow where we can find you when people want to
reach out to you after listening to thisepisode.
(13:09):
You can go to optifinancial.com.
That's our firm.
It's a boutique wealth management firm.
And also, you can find my book on Amazon orBarnes & Noble, wherever.
It's called Playing the Wealth Game.
Good information in this about learning themindset between checkers and chess and, you
(13:34):
know, complimentary consultations on ourwebsite.
People can just, you know, reach out to us andlet us try to help you.
And if we can, we can.
If it's a good fit, it's a good fit.
If it's not, you know, no harm, no foul.
I love it.
Thank you so much.
Please reach out to Freddie.
He's amazing.
He shares his wisdom about wealth, and I lovebooks as well.
(13:57):
I will check it.
This is the word.
I will check it first and then play chess, ofcourse.
Thank you so much.
I have one last question.
It is about your goals and intentions.
Do you set goals for yourself, and what is oneof your next projects?
My, my next projects are, buying an apartmentbuying apartment buildings.
(14:22):
But, I would say my goal for myself is just tocontinue helping my clients, continue building
a good client base, you know, especially peoplethat wanna play chess, people who, you know,
it's it's nice when you hear hear from yourclients how communicative you are, you answer
the phone, and that type that, you know, thattype of stuff.
(14:43):
And, you know, just continue building thisthis, you know, my firm to, to a great
reputable status in the marketplace.
Wow.
I love it.
Thank you so much for sharing.
Now it's time for your final thoughts to theaudience, please.
Well, I would say that successful people arethe people willing to do the things that they
(15:05):
don't want to do in order to get where you wantto be.
If you're, you know, one of the goals of thebook was to help people stop screaming at the
moon.
Why do the rich keep getting richer and othersnot?
It's because you're playing a different game.
And, you know, there's definitely a do as Isay, not as I do element in the financial
(15:25):
world.
So we need to be on the lookout for that.
And just don't, you know, follow what peopleare doing, not just what they're saying,
because there's a lot of people out there thatare getting very wealthy from teaching checkers
and then playing chess.
So, you know, just find a guide that's going tobe right for you.
(15:50):
I love this message.
Thank you so much.
This was a great interview.
Thank you.
Thanks for having me.
And see you in the next episode.
Thank you for listening to Inspired ChoiceToday.
I'm thrilled to have you on this journey ofgrowth and transformation.
Don't forget to hit follow or subscribe to stayconnected and never miss an episode.
(16:15):
And here's something special.
Grab your free 20-minute breakthrough sessionwith me.
It's designed to help you kick-start or levelup your business.
Just check out the show notes for more.
Until next time, keep making those inspiredchoices and see you in the next episode.
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