Dec. 4, 2025

Fall in Love with Your Money and Stop Dreading Tax Season with Kirsten Graham

Fall in Love with Your Money and Stop Dreading Tax Season with Kirsten Graham

In this episode of Collaborators Unite, Chuck Anderson speaks with bookkeeping expert Kirsten Graham about simplifying bookkeeping for entrepreneurs. They discuss the importance of outsourcing, understanding money mindset, and the common mistakes business owners make regarding their finances. Kirsten shares her journey into the bookkeeping world and emphasizes the need for support in managing finances effectively. The conversation highlights the benefits of hiring virtual assistants for bookkeeping tasks and the emotional aspects of financial management.

GUEST BIO:

Kirsten Graham is a business coach, outsourcing strategist, and financial-systems expert dedicated to helping entrepreneurs take back control of their time, money, and confidence. With a background that spans real estate, mortgage brokerage, and business ownership, Kirsten spent years mentoring self-employed clients who were overwhelmed by bookkeeping and operations. Alongside her business partner, Jeannie Wilson, she has helped hundreds of small businesses outsource key tasks, streamline their operations, and build supportive, affordable virtual teams. Today, Kirsten specializes in pairing business owners with highly trained, vetted bookkeeping virtual assistants—often for as little as $6–$7 per hour—so they can finally fall in love with their numbers, stay tax-ready, and grow profitably with ease.


CHAPTERS:

00:00 Introduction to Big Impact Entrepreneurship

02:08 Kirsten's Journey into Bookkeeping and Outsourcing

05:28 Understanding Money Mindset and Bookkeeping Challenges

09:45 The Importance of Trust in Financial Management

13:35 Common Mistakes Entrepreneurs Make with Bookkeeping

18:16 Taking Action: Next Steps for Entrepreneurs

20:23 The Unique Approach to Building Your Own Team

22:42 Final Thoughts and Encouragement


LINKS:

Visit: https://sixfigurebusinesscoaching.com to connect with Kirsten and her team, learn about her virtual assistant services, register for her bookkeeping masterclass, and explore the Marketing VA Advantage program.


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Until next time, keep moving forward!

Chuck Anderson,

Affiliate Management Expert + Investor + Mentor

https://AffiliateManagementExpert.com/

Speaker:

Hello and welcome back to the show.

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This is the Collaborators Unite podcast, Chuck Anderson here, your host.

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And this is the show for big impact entrepreneurs.

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And that's you because you want to not only make money with your business, but you wanna

make a big impact in the lives of your clients and your communities and maybe even the

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world.

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And in our conversations with uh fellow big impact entrepreneurs,

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or any entrepreneur for that matter, is the subject of how do I keep track of everything

uh to make my bookkeeping simple, my taxes simple, and do I really have to spend all of

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this money on that?

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so today I thought it'd be really cool to have an expert come and share with us her tips

and also how we can uh get the help that we need and not have to spend.

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a fortune doing it.

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So uh Kirsten Stewart is here with me today.

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Kirsten, Graham.

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Where did I get that from?

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In my brain, right?

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So I'll just, three, two, one.

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So today I have Kirsten Graham with me here today and she is an expert on these things and

we're gonna dive into this topic and you're gonna hear some things from her that you

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probably aren't hearing anywhere else.

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So Kirsten, welcome to the show.

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Chuck, thank you so much for having me.

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for all of you people who are thinking bookkeeping, no, it's boring, don't click away.

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Stick with us, we'll make it interesting and fun, promise.

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Yeah, and that's what I really loved about our initial conversation is bookkeeping can be

uh historically a boring topic.

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This will not be.

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And so I really love your fresh approach to all of this because it solves some problems.

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uh You know, I've always struggled with keeping track of everything and even uh sometimes

even with getting everything ready for taxes and making that as simple and as cost

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effective as possible.

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and it's usually not at the top of my priority list.

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uh which I've been told is something that a lot of entrepreneurs go through.

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uh So let's start with, tell everybody a little bit more about you and how did it come to

be that you're doing the work that you're doing now and we'll go from there.

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Sure, yeah, so my background's actually real estate.

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I started selling real estate in the late 80s.

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I moved to the mortgage side of the business.

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I eventually went on to own a mortgage company and a title company.

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And I did a lot of loans for self-employed people.

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And I would see their personal tax returns and I'd see their business tax returns.

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And then they would say, can I take you to lunch to pick your brain?

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And so I really started mentoring business owners for about a decade before I actually

started taking on coaching clients.

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So that's kind of my natural progression into business coaching.

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And then within that space of business coaching, what I realized is a lot of times we

don't need more courses or coaching.

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We just need help.

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need people to get stuff done for us.

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And that really led me down the path of outsourcing with one of my clients, Jeannie

Wilson, who is actually now my business partner.

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Her agency blew up really

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quickly and it's been 15, 16 years ago now, a long time ago.

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And I said, I read about outsourcing overseas, would you want to try that?

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And she said, okay, if you'll help me.

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And that took us down a rabbit hole of making lots and lots of mistakes and learning lots

of lessons.

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And, but realizing that, you know, small businesses, you know, and I'll say small under

500, under let's say under 5 million.

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You can get the support that you need very affordably so that you can keep your expenses

low and your cash flow and your profit margins high.

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And that's what I love about outsourcing.

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So initially we're really focused on marketing virtual assistants and helping our clients

outsource their marketing.

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And that's because that's Jeannie's expertise.

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But over the years I've helped law firms and bookkeeping companies and CPA firms and lots

of different industries hire different types of support.

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And

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Not too long ago, I started thinking about the bookkeeping companies that I help hire

bookkeepers for.

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Most of them are at $80 to $100 an hour.

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And a lot of business owners, they feel like they can't afford it because bookkeeping is

not always a priority.

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We often afford what we prioritize.

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But I thought, what if I could help the smaller business owners get really affordable

bookkeeping?

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We're talking like six, seven bucks an hour.

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And...

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help them with the process of falling in love with their money.

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So that's kind how we ended up here Chuck, a long story.

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Yeah, I love so much of that.

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I was at a conference last week and they talked about the accidental entrepreneur where we

kind of stumble upon the next good business idea.

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And I love how one thing leads to the next and now you find yourself here doing this.

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what I had to do a double take on the first time we chatted and for our audience's benefit

as well.

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Yeah, you really did say six to $7 an hour, right?

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And I'm like, really?

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Like, are you kidding me?

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Like that just sounds so low.

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And so, and as a business owner, I can tell you that the last thing on my mind that I like

to spend money on is, you know, adding up all the money that's already spent.

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so.

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Yes.

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ah how common of that is an issue and what are you hearing from people in terms of when

they come to you and you're working with them for the first time, what is their

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experience?

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What's happening out there?

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What are us entrepreneurs doing that are making this more difficult than it needs to be?

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The first thing I like to address is there's a lot of people out there teaching money

mindset, which I think is really important.

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You we all struggle with our mindset around money and finances.

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There can be a lot of shame and guilt around it, lack of education, financial literacy.

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There's just a lot of things that go into that.

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But one of the things I realized was you can't manifest more money.

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You can't grow a business bigger if you're afraid of your money or if you're sticking your

head in the sand.

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And so that was something that really connected when I was talking to some of the clients

because

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again.

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You need to kind of love your money.

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And sometimes that feels hard to do if you're having a bad month or a tight month.

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You know, we talk a lot about giving gratitude when you're paying your bills, you know, be

given a ton of gratitude when that money comes in because that money is, you know, your

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clients money.

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They're paying you for value.

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They're paying you for your services and to be grateful for the opportunity to work with

those clients.

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So we try to focus on the whole concept of money.

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And then the other thing I think is really important is we think about unique abilities,

right?

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You do what you do because it's your unique ability.

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uh

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You know, I do what I do.

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And I know this is really hard to understand, but there are crazy people out there that

love bookkeeping.

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Like that's their unique ability.

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You know, so, you know, the bookkeepers that we have, they're all in the Philippines.

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They have either degrees in accounting or finance.

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You know, they're Quickbook Zero certified.

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They've got a minimum of three years experience in bookkeeping.

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But more importantly, that's their jam.

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Like they love bookkeeping and they're passionate about helping you understand your

numbers and strategize how you

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could make your offers more profitable because they see things that we don't always see,

which I think is amazing.

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Yeah, I love that.

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Well, first of all, that that passion for the work.

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I think I have to be grateful for that because uh I do not have a passion for that kind of

work.

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And I would much rather have someone else do it.

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And the fact that I love to because I've done outsourcing before and, uh you know, hiring

from the Philippines or from other countries.

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And uh and so one of the things that uh

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is always been a challenge is getting the people who are super skilled.

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So I love your vetting process where you're getting the people who are, they're not new at

this.

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They didn't just put up an ad saying, yeah, I'll do bookkeeping.

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uh They actually know what they're doing.

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Yeah, and that was a process.

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Like I said, I was really lucky because I do have several clients that own bookkeeping

agencies and a small CPA firm and I've hired bookkeepers for them because I'm not a

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bookkeeper.

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So I was able to really learn the back end of what was so important.

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And, you know, we have a really detailed process we go through.

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You always want to hire slowly, fire quickly.

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And so we spend a great deal of time on the front end, making sure that we are getting the

right team members for us and for our clients.

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The other thing is we are not an outsourcing agency.

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So we're not marking up the labor of the virtual assistants.

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You know, our clients pay us a flat fee at the beginning.

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You know, we educate them on different bookkeeping softwares.

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We help them understand different things that they can write off and things to consider.

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And then we pair them with the right bookkeeping virtual assistant for them.

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And that person joins their team.

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You know, and if you're behind on your bookkeeping, which, you know, we've got a couple of

clients that we're going all the way back to 2022.

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They're getting they're getting caught up.

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You know, your bookkeeper is going to be working with you a lot.

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of hours, but again at six, seven bucks an hour, that's affordable.

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But most of our clients, once they're up to date, their bookkeeping is usually around four

to five hours a month.

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So it's not a lot of time because you have someone, again, it's what they do, it's what

they do well, they create a structure around it, they get it done quickly, they meet with

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you, they go over your numbers, and then you know where everything is at every given

moment.

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So it really is magical.

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uh The other thing is, I always like to tell people, like Chuck, you hired one of our

bookkeeping virtual

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assistance.

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I don't know anything about your finances ever.

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You know, I might check in and say, hey, did you connect with Chuck?

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How are things going?

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You know, just to check in on that relationship.

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But I never ask anything about what's going on with your finances because I feel like

there's a lot of emotions that we have around money.

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And so I want to make sure everyone understands that there are ways to keep your data

secure when working with someone overseas.

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And there's also the importance of feeling like the person that's on your team, you trust

them to become your, you know, your

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valid your valued team member but also your confidant and advisor because you know numbers

is their specialty.

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You know, I love what you just said there because I think as someone who has uh worked

through the situation before of having several years to make up and

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There's a certain amount of stigma that comes along with that embarrassment.

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Like, my God, I don't want anyone to know that this is happening.

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And I remember talking to an accountant one time and he said like, look, don't worry about

it.

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You would be surprised how common this is.

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you're in good company because there's other business owners and names you would recognize

that struggle with this very thing.

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Is that what you're noticing as well?

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Absolutely.

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And I don't know why we have so much guilt and shame around it.

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I said, most, you know, it's like most people that that's the thing that's going to get

put on the very back, back, back, back, back burner.

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It's going to get done, you know, if we have any bandwidth.

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And then we all are fearful of getting audited, you know.

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And here's what I see happen.

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You know, we're in the U.S.

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and you're in Canada, but

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You know, we know January, we need to start getting our things together for tax time.

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And we know when we need to file our extensions or file our taxes, but we don't think

about the amount of mental and emotional bandwidth that we use up worrying about it.

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You know, how awesome, you know, does it feel to walk into your CPA at the end of January,

early February and say, here's all of my information.

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It's ready to file my taxes.

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call me when they're done.

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You know, to be able to have that power and to not have that stress, to not have that

anxiety, that's my ultimate goal for our clients.

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Yeah, that sounds amazing.

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And I can tell you that for us, there's only been one year out of the last 10 where that's

been the case.

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And it is a good feeling.

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And then the other years, you're kind of going, yeah, I forgot.

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Right?

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What a great feeling.

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And it just needs to be systematized and out of my hands.

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I, so many other founders and business owners, I think feel the same way, right?

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Absolutely.

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Yeah, but if you think about it, let's talk like let's say you want to buy a house, you

know, they want to see your tax returns What happens if you get audited?

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You know, I mean that can waste an entire month or two of your life if you get audited and

you're very unorganized Someone said the other day which is true in the US our software

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and our hardware is antiquated and the IRS is short-staffed I a hundred percent agree with

that

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But let's fast forward.

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They update their software, they update their hardware.

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I don't think there's anywhere in our tax code that says we have to be audited by a

person.

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With AI, they could probably audit every single person every single year if they wanted to

within the next two to three years.

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So I think now more than ever, it's going to be important for us to figure out how to have

those things, how to have our ducks in a row so we don't have to worry about it.

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And we talk a lot about time management and energy management.

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When you hear people talking about energy management,

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Just know that when you're not doing something, in this case you're bookkeeping, it's

sucking away your energy.

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Not even in your conscious mind all the time, but in your subconscious mind.

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And so it's a miracle when you could have somebody who loves doing the stuff we hate do it

for you at a very affordable rate.

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you know, but it is what's human nature.

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We want to fight against what we don't like to do.

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Yeah, for sure.

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And I think there's always that part of us that knows.

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You just know that that part isn't taken care of.

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And it's not going away.

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It's not going away.

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It's gonna be a reality.

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And uh you're either ready for January or you're scrambling to finish it in April, which

has been so many years that we've done.

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uh What are some of the uh mistakes that you see

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business owners making that if they just did it, you know, if they just shifted into this

or that, or, you know, just change it, it's not, usually what I find is it's not as bad as

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you think it was.

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And so once you kind of, I'm like, oh, well, I don't understand like why this was so hard.

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But what are some of the common mistakes that you see people are making that make it

harder than it needs to be?

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Yeah, so first of all, business owners miss a lot of write-offs.

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So we're often paying more taxes than we need to because we're not strategizing.

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You think about your larger companies.

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They are strategizing to figure out every single tax advantage that they can have.

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And that's because they have a team of people that do that.

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The CFO is in charge of that, making sure that happens.

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So for us, it's very easy to forget to write things off.

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Forget to your home office.

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Maybe miss some mileage.

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Not take all the write-offs where you went to a conference because you didn't keep your

receipts or

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whatever.

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So by not being organized we're leaving money on the table.

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So that's most important.

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The second thing where I think we mess up is not understanding if we don't know our

numbers we don't always know how to price our offers.

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know in a lot of the online space there's a lot of conversation around what do I charge.

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The reality is once you understand your numbers, it really helps you see more of your

value and it helps you price your services.

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But there's this rule, this concept, that if I tell you, Chuck, I'm going to do something,

I'm most likely going to do it.

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If I tell myself I'm gonna do something, in theory I should, but I may not.

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And also as human beings, like working collaboratively.

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generally like, especially when we're doing something we don't want to do, it's always a

lot more fun to do it with a friend.

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You've got to clean out your closet, have your girlfriend come over, pour some wine and

get your closet cleaned out with someone there helping you.

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That's what we have found with having a bookkeeping VA is that you now have this person on

your team.

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If you said that you're going to get them a statement by Friday, you get them a statement.

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And it's just a different mindset when you know that you own a business and you have team

members and you need to get work to them.

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because you're gonna pay them.

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And I think that was the biggest thing that changed so many people's realities was

understanding what it was like to have, I like to use the word support.

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Having support and doing something that you don't necessarily enjoy doing, it's not

terribly difficult, but you just would rather put it off.

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But if you know that Chuck's waiting for it, you're gonna send that over to him.

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If you told Chuck you're gonna meet with him at the end of the month, you're gonna meet

with Chuck, right?

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So that concept was really eye-opening.

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I really love that.

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in a lot of ways, you're really setting yourself up to succeed and to make it uh easier.

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uh It's funny, because we do that already with project management and event management and

our affiliate management.

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We collaborate with team members.

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have them.

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And it's so much, when my team needs something, I make sure that they get it, because I

don't want them to stop.

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I don't want them to be paying them to sit there waiting for me.

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And so sounds like this, it's not about the software.

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It's not about some magic tool.

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It's about having another human to collaborate with so that it's more likely to get done.

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and some accountability, but you're also meeting with someone again who is excited to do

the job.

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You know, I don't know about you, but if I'm meeting with one of our marketing virtual

assistants and they're excited about edits that they've done or, you know, graphics or

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design that they've created, you can't help but get excited when they're showing it to you

and we're talking about it because they put their heart and soul into it.

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They're so passionate about it.

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So it's contagious.

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That can be true also with your bookkeeping because here's someone who's super passionate

about the numbers and going over them with you.

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And so it really does just shift

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things having someone else to be accountable to, but also to have someone else to support

you in learning really how to make your business more profitable and how to increase your

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cash flow.

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And when you do that, this is the other thing that I've found really exciting, is when our

clients are up to date on everything, then they start thinking about, wanna, you know,

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we've got a couple of people say, I wanna start offering affiliate marketing for my

courses and coaching.

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because they start to see, well, if I can have other people out marketing my services,

then that's a great, very affordable way to bring in new clients.

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But again, sometimes when you're so busy and you're so muddled down, you don't think about

it.

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Or they start thinking about how can I have more passive income?

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How can I increase cash flow that doesn't always involve me being in every situation?

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My hands don't have to be in everything.

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How can I do that to start bringing in some money where I can be hands off in my business?

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And those are things that I think are really powerful.

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Yeah, absolutely.

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I love all of that.

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And I wanna talk a little bit about, you know, we talked about, you know, obviously what

you do and we talked about some of the mistakes that those of us who are business owners

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make and it's a very common thing.

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So we don't have to feel embarrassed or about it anymore.

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What are the next steps?

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What should we be thinking about?

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and uh taking the next steps towards so that, you know, if we have had that problem, we

don't have that problem anymore.

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And I love what you just said about going into uh January or any tax season and just being

to say, here you go, and everything's ready to go.

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Yeah, so I think the first thing is realizing you deserve the support.

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You as a business owner do not have to wear every single hat.

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You deserve to hire people with great expertise to do things for you.

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So that's the first thing.

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Acknowledging that we don't have to know everything to hire someone.

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I mean, I took my car to the shop the other day.

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I didn't need to know how to fix my car to get it fixed.

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I hired the guy who fixed it, right?

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So, you know, it's letting go of a little bit of control.

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or perceive control because it's really not control when you're just scrambling at the end

of the year to throw something together.

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It's actually less control than if you have someone who's trained supporting you.

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So that would be the other thing is realizing that you deserve the support.

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There are people who are really great at what they're doing and then you have to decide,

am I going to take a little bit of my time to get this up and running because nothing is a

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magic wand.

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know, Chuck, if your bookkeeping virtual assistant started with you next week, you know,

you're deciding what bookkeeping software you're going to

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use.

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You're setting that up.

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You're making sure to figure out are you going to put your documents in Dropbox or Google

Drive, you know, so we're going to talk about all of those things and then you have to

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start taking action to get them the things that they need so that they can move forward.

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But what happens is once that initial start process happens and you start having those

meetings, then everything changes because of the accountability and because of the fact

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that you're outsourcing this, you're having someone on your team who is excited to do that

particular work.

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Hmm.

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Yeah, that sounds really, really good.

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And it would be just so nice to just have that system where you know that it's done and

not really have to think about it until until it's time to print it off and and and take

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it to the accountant for sure.

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um So there's I love the uniqueness of an.

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of your offer and how this works.

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And I'd like to hear a little bit more from you because so many agencies are, you go to

them and you're using their people and they're assigning it to their team.

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But you have this really unique approach where you're helping business owners find their

own team member.

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Like they're not having to go through you.

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So talk a little bit more about how this works and.

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and just so that our audience knows.

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And I'm gonna encourage them afterwards to connect with you so that they can learn more.

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Sure, yeah.

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So when Jeannie and I first started, our first offer was the Marketing V Advantage where

we help clients who want to start a YouTube channel or a podcast.

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We help them hire a virtual assistant who takes care of all of those things in the back

end of that.

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What surprised me, Chuck, more than anything else was when the clients started working

with their virtual assistant, they would still come to our weekly coaching calls to ask

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questions about their content or about managing their new VA.

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What shocked me the most was people saying things like, feel like a real business owner

now.

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I had no idea how isolated and lonely I was in my business.

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I had no idea how much I was beating myself up because I couldn't get everything done.

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And now I have this person working for me.

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15, 20 hours a week and I'm seeing everything that they're doing and I don't know how I

ever thought I could do all of that and everything else that's on my plate.

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So that was an aha moment for us is seeing them feel so empowered by having a team member.

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And that's something that how we feel as a business owner, our confidence, not our ego,

but our confidence has a big impact on how successful we are.

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And so when you can start to build a team again, a team doesn't mean you someone 40 hours

a week.

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It can mean someone four or five hours a month or five or six hours a week, whatever you

need.

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But when you start to build that team of experts who are doing things for you, it

completely shifts that business owner's level of confidence.

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It increases their time and availability mentally, emotionally, and physically time

available so that they can do bigger things.

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They can make better decisions.

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And that was really the reason why we didn't want to be the middle man.

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And I get this all the time when I'm on interviews, but you're leaving so much money on

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table.

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We are like most agencies, they mark up the labor, they take the difference.

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But again, for us, it's really thinking about how do we want to impact the world, what's

important to us.

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And for me, it's helping that business owner really start to build the team that they

deserve to have and learn that they can be amazing leaders.

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You know, we manage tasks, we lead people.

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And sometimes, especially women, think that they're not great leaders or they're not great

at managing.

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And that's simply not true.

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They often haven't been given the tools or the skills.

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that they need to be successful and that's one of the things that we're really passionate

about providing.

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I love all of that.

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Well, let's give everybody a way to connect with you because I think that definitely we

have people leaning in and going, know, bookkeeping, not my thing.

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I just want to focus on what I do.

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And you can help them to be organized without really having to, uh you know, become

skilled at it themselves.

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You know, I'm not a skilled bookkeeper.

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do not love doing it.

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I love the idea of giving it to someone who loves doing it.

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And yes, these people do exist.

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So what is the best way to connect with you?

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And we'll make sure we put all the links beneath the video so that people can reach out to

you.

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the first thing we'll say is just go to our website, which is

sixfigurebusinesscoaching.com.

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We are offering master classes for this program.

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As we get closer to tax season, we'll start offering two a month.

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So go there and then you can sign up for one of the master classes if you like.

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And you can also learn more about the different types of virtual assistance that we

provide for our clients if you're interested in other support in your business.

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Well, that sounds like something we should do right away and get on our calendar so that

that happens.

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So uh check beneath this video.

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If you're watching this on video, uh all of uh Kristen's links are right there.

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Click the link, go and register for the masterclass.

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Get it on your calendar.

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And if you're listening to this on a podcast, just open up your phone and all of the links

are there as well.

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uh Sounds like a great next step and I always

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encourage people to think about that as they're listening to this about what is my next

step?

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What is the next thing I can do that makes this easier?

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So definitely we just scratched the surface in the small amount of time that we have on a

podcast like this, but hopefully it has awakened some people's awareness in terms of

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you know what, this doesn't have to be as hard and it can be easy and I don't have to

spend a fortune doing it.

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And I love that that's what you do.

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ah So as we sign off, anything else that you want people to know about bookkeeping,

accounting, taxes before we run out of time.

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Well Chuck, first of I to thank you so much for having me.

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I really enjoyed talking with you today and you're always like this burst of energy.

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So always get excited when we have conversations.

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Yeah, I just want to let people know that you you started a business to be successful and

don't let the one thing that can really get in the way of you truly being successful,

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which is a solid financial foundation, get in the way.

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Yeah, for sure.

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Yeah, don't let that get in the way.

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there's so many other things that can get in the way as well.

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So, Kirsten, thank you.

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I really appreciate this.

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I look forward to attending your uh webinar.

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And I encourage our audience to click the link and register for it as well.

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And even if you already have your bookkeeping systems, who knows what you're gonna learn?

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I learned something in the first five minutes of meeting you.

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oh

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ah And so uh who else who knows what else we're gonna learn from from attending that So,

thank you uh any final advice words of wisdom before we sign off

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I just love, mean, first of all, gratitude, because we're recording this the day before

Thanksgiving in the US.

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And, you know, I feel like I up every day so thankful that I get to have a business, that

I get to run my schedule, that I get to work with amazing people and collaborate with

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people like you.

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And sometimes I think we can get so busy and so in the weeds that we forget just to think

about how lucky we are and how privileged we are to be able to own and build our

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businesses.

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Be grateful.

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And those are beautiful words to end this episode by Kirsten, thank you so much.

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To our audience, thank you as well.

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Hopefully this has been time well spent and if you're still listening right now, that

means this is resonating with you.

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The next thing I'd like you to do is click the link beneath this video and register and

connect with Kirsten and go and learn.

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uh You don't even know what you don't know.

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And so remember, you might be one collaboration away from the big breakthrough that you

need in your business so you can make a bigger impact, so you can focus on your gifts, so

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you can focus on the things that you're doing.

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And perhaps this is that collaboration opportunity.

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So go and do that right now.

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And remember that there's going to be obstacles along the way and there's going to be

challenges.

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There's no

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problem or challenge that cannot be solved.

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And it's usually by connecting with another person and not a tactic.

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And we did talk about that a little bit here today.

398

00:29:19,167 --> 00:29:23,322

um So don't let the obstacles get in the way.

399

00:29:23,322 --> 00:29:25,214

The only way to fail is to quit.

400

00:29:25,214 --> 00:29:28,959

So keep moving forward, everyone, and we'll see you on the next one.

401

00:29:28,959 --> 00:29:29,909

Thank you.

402

00:29:32,078 --> 00:29:32,943

stop.