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Five Conversations Every Business Owner Needs to Have
Episode 2730th April 2026 • The Bucket List Accountant • David Patterson
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In this episode, David Patterson walks through the five essential conversations every business owner needs to have — not just with their accountant, but with themselves, their family, and the people who matter most. These aren't just financial conversations; they're life conversations that lay the foundation for building a business that truly serves the life you want to live.

David shares why most business owners drift through their working lives without ever articulating what they actually want, and how simply writing down your goals gives them a life of their own. From aligning family goals to planning a business exit that isn't defined by the word "retirement," this episode offers a powerful framework for living and working with purpose and intention.

What You'll Learn: • Why getting your personal goals out of your head and onto paper changes everything • How to align your goals with your family's goals so the business works for everyone • Why money conversations are easier when everyone understands the purpose behind them • How to build your business to be exit-ready from the earliest stages • Why replacing "retirement" with "the next phase of life" leads to better planning and fewer regrets

Connect with The Bucket List Accountant:

David Patterson on LinkedIn: https://www.linkedin.com/in/bucketlistaccountant/

Website: https://www.bucketlistaccountant.com.au/ Because financial freedom shouldn't mean sacrificing your wildest dreams.

Subscribe now and get ready to take control of your money and your life!

Co-host: Anthony Perl

Produced by: Podcasts Done for You

Hashtags: #BucketList #BusinessOwners #FinancialPlanning #ExitStrategy #LifeGoals #SmallBusiness #NoRegrets

Transcripts

Anthony Perl:

The five conversations every business owner needs to have.

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Join the Bucket list accountant himself,

David Patterson, as we explore the

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essential discussions required to align

your business with your personal life.

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Learn how to identify and

articulate your true personal goals.

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Discover the importance of family

alignment and financial clarity,

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and gain insights into creating an

exit strategy that supports a life.

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With no regrets.

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This episode provides a framework for

moving from drifting to designing a

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future filled with meaningful memories.

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I'm your co-host, Anthony Pearl.

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Let's get into making

your bucket list happen.

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David, I know this is something

that you've raised and I want

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to explore this with you.

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Five conversations every

business owner needs to have.

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So probably hit me up from the start.

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What are those five conversations?

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David Patterson: Yes, I

did say that, didn't I?

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Uh, so I think the first one

for me is about your goals.

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So conversation one is about your

goals and, and knowing what you want.

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I'll just summarize these

and we can go back, Anthony.

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I guess the second conversation

is around your family, your goals,

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and your family's goals aligned.

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Do you know what each other wants, and

is it sort of all working well together?

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The third kind of

conversation is around money.

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How much do you need?

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A lot of people don't

like talking about money.

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How much do you need to do the

things that you wanna do, your own

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goals, family goals, et cetera.

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The fourth kind of conversation

is around exiting your business

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and how are you gonna do that?

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What's your plan?

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And then the, the last conversation

for me, which is probably the really

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important one, is that the people

being able to get to the end of their

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business life and their life with no

regrets or as fewer regrets as possible,

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but ultimately with no regrets.

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You know?

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So I think they're the five big

conversations that people should have

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and should be front of mind all the time.

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Anthony Perl: But it just reminds me

that an ex-girlfriend of mine, many,

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many years ago, I think she remember, she

said to me, regret is a wasted emotion.

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And it's very true.

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You don't want to go with

regrets, that's for sure.

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David Patterson: No, and

and just on, just, sorry.

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Just on that, Anthony,

I remember when I was.

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I was about 2021 and I'd worked

for this guy for five years

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straight outta high school.

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Worked for him for five years.

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And part of his plan for me

was that I continue working.

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'cause in those early days I

wasn't earning much money 'cause

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I was learning what I was doing.

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And I came to him as soon as I finished

uni and said, I'm resigning 'cause I'm,

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I wanna go and travel and work overseas.

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And I thought he was gonna

get really angry at me, and

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he said, that is magnificent.

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Go for it.

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He said, that's one thing that I wish

I had have done when I was your age.

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And it's kind of a conversation

I've, that I had that has stuck

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with me all the way through.

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And that he, I mean, he would've

been in his, I don't know, late

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fifties and hadn't done that trip.

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And it was one of the things

that he'd regretted doing that

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he hadn't taken it earlier.

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So I went in there thinking

I was gonna be sort of.

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Blasted and he sort of said, go for it.

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Well done.

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So, yeah, no regrets is a key

focus for me in particular.

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Anthony Perl: It's a wonderful thing

that we can carry forward to our kids.

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I know my daughter came to me and said.

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I want to go and see, and I won't say who.

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Someone in London in a concert,

and you know, the sensible father

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from me says, save your money.

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You can put a deposit on

something and save for the future.

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But the other part is you're

not gonna get that back.

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She's single, she's able to do it.

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She's got the money to be able to,

or she's working towards having

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the money to be able to do it.

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Why not?

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Because,

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David Patterson: mm-hmm.

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Anthony Perl: Yes, it's

X amount of dollars.

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Yes, it could be a help towards

a deposit, but by the same token,

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it's something you want to do.

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Why not do it when you can do it?

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So, you know, being able to get to

that with conversation is so important.

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Right.

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David Patterson: Yeah.

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A hundred percent.

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It is.

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And the biggest thing for me that

it does, and I think we might

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have spoken about this before,

is it's the memory it creates.

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That memory, I'm not sure how old

your daughter is, but that memory

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goes from now all the way through.

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You know, she'll talk about that.

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Something will come up in conversation

in 20 years time and she'll say, when

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I was whatever age, I went over to

London and I saw this person perform

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and it just creates the memory.

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I talk about stuff that I

was doing back when I was.

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22, 23, 24 overseas, and it comes back

to you as fresh as if it was last week.

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I wish it was last week, but the

memories are phenomenal, you know,

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and that's one of the important

things about doing these things when

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you can at the early age because

of those memories that they create.

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Anthony Perl: So seeing the importance of

that fifth conversation, let's go back to

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the beginning, to the first conversation.

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David Patterson: Yep.

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Anthony Perl: So how do you start that?

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David Patterson: Well, the start

of, it's really quite simple.

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It's just asking the client the question.

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The, the hard part of it is that a lot of

people haven't been asked that question.

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They've got a lot of thoughts running

around in their heads, but they

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haven't really articulated a lot

of them about what their goals are.

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And I did it for ages.

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You know, you kind of just.

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You're drifting through life a

little bit and just hoping that

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things will happen down the track.

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So asking the people about what their

goals are, it starts as a a bit of

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a stunted conversation because they

don't have it readily at hand, but

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over the time, the things that they

want to do start to grow and it start

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to expand and their imagination of

the things they wanna do gets greater

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and they start to worry less about

what their goals are and what other

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people think of their goals, you know?

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So it's a growing sort of

organism that gets built and.

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Some of the things that they initially

thought wouldn't be achievable.

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Put 'em down, write 'em down.

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Let's work on how they

can be achievable first.

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And if we work through it and

you still can't do it, then

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some things you can't do.

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But let's not just

discount 'em completely.

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Let's, let's put all

our goals down on paper.

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And this is the important part,

getting them down on paper.

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I think it's really important not

to have them just in your head

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because they start to get alive for

their own once you write them down.

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And it gives everything

else a lot more clarity.

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You know, it gives you the purpose

of your business, a lot more clarity.

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It gives everything a lot more clarity

If you know what your personal goals are.

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Anthony Perl: So I know from a practical

point of view, it's easy enough to

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write them down, but that relationship

for people to be able to give that to

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you because they can be quite personal

and there's a feeling of being judged

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David Patterson: mm-hmm.

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Anthony Perl: When you are

having them, you know, because

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David Patterson: mm-hmm.

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Anthony Perl: You know, I've

got a friend who drives a really

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expensive car and that was a goal

of his, to have that expensive car.

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It's not my goal.

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I'm okay.

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I'm okay having a drive in it the once.

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David Patterson: Yep.

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Anthony Perl: But I don't

need that car particularly.

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David Patterson: Yep.

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Anthony Perl: And, but that's okay.

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Right?

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David Patterson: Yep.

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Anthony Perl: But you've gotta actually

build that relationship, don't you?

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And that trust factor for people

to actually share legitimately

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what their heart is in their

goals, not what they believe other

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people think their goals should be.

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A

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David Patterson: hundred percent.

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A hundred percent.

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If I made a new client for the very

first time, they're not spilling

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all of their sort of deeply personal

goals to me at that point in time.

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They're giving me a surface list of the

things that they wanna do, which could

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be, you know, I wanna own this flash car,

I wanna do this holiday, I want to do.

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You need to build the relationship

before they open up with more personal

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goals that they wanna do, and even some

silly goals that other people might not

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think's that big a thing for that person.

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That's a big goal to have.

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Anthony Perl: So we've got the goals down.

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They've come to you with that.

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That's conversation one.

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David Patterson: Yep.

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Anthony Perl: What's the progress now?

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How do you engage with that?

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And then just out of interest, I mean,

how long does that process take before

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you then get to conversation Two.

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David Patterson: Yeah, that conversation

can vary depending on the person.

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Someone might jump into this really

quick and that conversation might

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take less within a couple of days.

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It might take a couple of weeks.

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It depends on the personality of the

person and how quick they are to trust

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and how quick they are to sort of

believe that they're not gonna be judged

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on the things that they write down.

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Once that's done, and it's an important

part for me to get that understanding

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and for them to have their understanding

of their family goals as well.

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It's well enough for me to have the

things that I wanna do, but I need

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to have an understanding of what my

wife wants to do as well through life

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and what my kids wanna do as well,

and where there's a cross between

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our goals, we can join them together.

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But also understand that at certain points

in time, Tammy's gonna want to go off

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and do something that's not on my list.

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But if I don't have that understanding

of what her goals are, I'm just working

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away to achieve my goals, which,

you know, doesn't help her at all.

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Anthony Perl: You've gone

through the goals, conversation

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two, take me through that.

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David Patterson: Conversation One and

Conversation two are virtually the

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same, just with the different people.

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So conversation ones with the business

owner or the main purpose of the business.

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And conversation two is

with the rest of the family.

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Same conversation, just

with different people.

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And for me, I.

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It's important to understand what both

lots of goals are so that as we're

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working through the business and working

through the improvement in the business

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and getting the business in a position

to achieve the goals, if only, no one

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lot of goals that what we're doing in

the business could be detrimental to

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the other goals, and having those shared

goals as well also helps create the

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interest in the business from everyone.

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Because they know that the

business performance is gonna

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help them all achieve their goals.

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Anthony Perl: This podcast is brought

to you by bucket list accounting.com

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au.

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Speak to David Patterson and his team

if you want to take better control of

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your life and business, helping small

business owners like you be successful

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designing the life of your dreams.

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Go to bucket list accounting.com

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au or check out the show

notes for more information.

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Now back to the program.

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That's the important

bridge there, isn't it?

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That it is that level of shared interest

in the business because conversation

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three, as you say, is about money.

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David Patterson: Mm-hmm.

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And

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Anthony Perl: money

comes from the business.

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So if there's not a relationship there,

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David Patterson: mm-hmm.

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Anthony Perl: It's very hard for

that one to flow into the other.

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David Patterson: Absolutely.

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And it also gives you a, a sense of

understanding if there's periods of time

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where the business owner has to spend

more time in the business doing work

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or whatever, because they know that the

reason they're doing this is so that, that

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we as a family or individuals or whatever,

we're able to do these other things and

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understand that there's a sacrifice that

sometimes has to be made for a period

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of time to be able to achieve the goals.

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And if there's this shared understanding.

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There's a more of an understanding

behind that sense that every now and then

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there's a little bit of additional time

has to be spent in the business to make

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sure it is doing what it needs to do.

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Anthony Perl: So we've

now got the goals sorted.

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We've got an idea on the money.

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Next conversation exiting.

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Because it's a big leak though, isn't

it, for, it's an important conversation.

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But how early is that conversation needs

to be had, given that it's about exiting?

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And some of the businesses that I imagine

that you are talking to might have

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people that might be in their thirties,

their forties, even in their fifties.

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And the, the idea of exiting and

potentially if that means retiring,

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exiting, doesn't have to mean retiring.

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David Patterson: No.

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Anthony Perl: But that could

feel like it's a long way away.

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So how important is that

conversation to have early on,

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and what does that look like?

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David Patterson: I think it's important

to start the conversation early on just to

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get a feel for what the expectation or the

idea of the business owner is and fitting

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around some of their goals as well.

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Some of their bigger goals to make

sure that the exit strategy is in

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place so that you know, they have

the time and their money to be

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able to do some of these things.

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But I've seen a lot of businesses

that just assume that at some

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point in time they're gonna be

able to sell their business for

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enough money to be able to retire.

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Which there's just no planning there.

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So you need to be sort of working towards

this almost from day one, I think not

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as much in the early days, but you still

need to be building these things in so

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that the business can be sale ready sort

of at a point in time because there's

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an opportunity that pops up along

the way and you are not ready for it.

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You know?

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It could be the opportunity of a lifetime,

but if you haven't worked on the business

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and built it in a way that can be sold,

you might miss out on a great opportunity.

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And there's also.

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Working on this so that you

maximize the sale value.

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You know, so that putting the things in

place and some of these things take a

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period of time to, to put in place and

just giving yourself the time to be able

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to get the business to a point where it's

big enough and profitable enough that

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it'll give you the money that you need.

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Or would like to retire on.

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And part of knowing how much you need

goes back to conversations one or two.

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Having an understanding of what your goals

are and what it is you want to achieve

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in life gives you that feel of how much

money you're gonna need, and so what your

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business needs to be worth and everything

else so that you can do those things.

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One of the big conversations that

accountants and financial planners

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will have with people, or one of

the biggest questions they ask is,

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how much money do I need to retire?

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Possible to answer because you

need to know what do you wanna do?

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What do you wanna do in retirement?

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What?

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And not even retirement.

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What do you wanna do leading up to that?

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What are the things you wanna do?

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How much are those things gonna cost?

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Do you want steak seven nights a week?

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Do you want sausages?

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What's your lifestyle?

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What sort of things do you wanna do?

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So the three kind of working

together, or the four kind of working

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together to create a life that you

can achieve and not just hope for.

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I

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Anthony Perl: think that's so

important and I want to go back to

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a point I made a little bit before

with this is in regards to exiting.

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Exiting doesn't have to mean retiring.

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Exiting can be a means to an end to

achieving more of those earlier goals.

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You might realize that the business

is only going to be worth so much.

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At any given point, you might sell it.

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So if it's not bringing you the

joy, if it's not bringing you the

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possibilities, if it's not bringing

you the opportunity to reach the levels

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you want, then it may be we need an

exit strategy that might be sooner

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David Patterson: Yep.

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Anthony Perl: Than 20 years down the

track when you're ready to retire.

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David Patterson: Yes.

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Anthony Perl: And look at what the

next steps might be from there.

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So that exiting conversation

isn't always about retirement.

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David Patterson: No, and one of

the things that I'm trying to steer

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away from is the word retirement.

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I think the word retirement has, in my

mind, it's a, a negative connotation.

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It's not retirement, it's

just the next phase of life.

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So you're doing these things

because a lot of people say.

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I'll do that when I retire.

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I'll do this when I retire.

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I think we need to get rid of that word

and just have them as different phases

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of life and so they can kind of merge in

together a little bit more so that you

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can still do some of the things you wanna

do while you're working, but then the,

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the sale or the transfer of your business

helps fund that next phase of your life.

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Anthony Perl: So now we come back

to the conversation that we sort of

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started this with, but is the end

conversation is living with no regrets.

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So how easy is it to have that

kind of a conversation and when

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do you have that conversation?

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Because based on what we've just

been saying, that is almost an

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ongoing one that you want to have.

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David Patterson: Absolutely.

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It's a continual one, and

these things change over time.

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There's no doubt about it.

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But just having a clear understanding

of what your goals are and being

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prepared to work towards them and

don't just hope that they happen,

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work towards making them happen.

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And I keep saying to

the end, but you know.

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Past selling your business and past doing

all the things you wanna do when you're

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kinda sitting there, if you're sitting

there having your last meal, if you

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could plan that, you want to be able to

sit there and go, everything I wanted to

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do, I did, and at least know that of the

things that you didn't get to do, there

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were reasons why you couldn't do them,

and you pursued it as hard as you could

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to make sure that you could do them.

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There's some things that you won't

be able to do, but as long as you've

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worked through it and attacked them

as hard as you could and then gone.

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I can't, you won't have the

regret at the end of the day.

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Whereas if give up on it right at

the start, that's when you'll have

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the regret at the end of the day.

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Anthony Perl: A few important

things as we finish up this episode

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of the Bucket List Accountant.

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Remember, financial freedom doesn't

mean sacrificing your wildest dreams.

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It means making them happen

with smart planning and purpose.

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Don't forget to download the playbook

from this episode via the link.

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In the show notes to help you

put these insights into action.

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We'd also love to hear from you,

so please leave a comment where

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you are listening to this podcast.

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It's your feedback helps

us shape future episodes.

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Make sure you join us for our next

episode where we dive into the topic.

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Every entrepreneur needs to hear

framing your business as its own entity.

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We'll be exploring how to define a

bucket list for your business and more

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importantly, exactly how to fund it so it

can fuel your personal lifestyle goals.

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Connect with David Patterson on LinkedIn

or via bucket list accountant.com

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au.

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To learn more about aligning your

finances with your life goals.

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This podcast is produced by my

team at podcast done for you.com

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au giving voice to business

leaders brilliance.

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If you found value in today's episode,

please like, share, and subscribe

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so you never miss a conversation.

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I'm Anthony Pearl.

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Until next time, keep making

your bucket list happen.

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