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Start Your Founders GANG with Dennis McCurdy (stage 2) - Ep. 425
Episode 4251st September 2026 • The Start, Scale & Succeed Podcast • Scott Ritzheimer
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In this empowering episode, Dennis McCurdy, Principal Owner of McCurdy & Andrew Investments, shares why going it alone as a solopreneur leads to the Valley of Dead Dreams and how accountability changes everything. If you’re grinding alone and watching your best ideas collect dust, you won’t want to miss it.

You will discover:

- Why you need a selective “gang” that will tell you the truth and push you forward

- How to choose accountability partners who show up and call you on your stuff

- What makes peer accountability more powerful than family or friends for growth

This episode is ideal for for Founders, Owners, and CEOs in stage 2 of The Founder's Evolution. Not sure which stage you're in? Find out for free in less than 10 minutes at https://www.scalearchitects.com/founders/quiz

Dennis McCurdy transformed his life from graduating near the bottom of his high school class and sleeping on an office couch to achieving a seven-figure net worth. Following his military service, he built eight businesses, managed 29 properties, authored four books, and led mastermind groups for over a decade. He teaches that mindset, accountability, and strong relationships drive true achievement. He is the author of the book Unleash the Power of Connection. He actively runs personal development workshops to help others reframe their failures into fuel for growth. He consistently proves that strong network connections and daily discipline directly accelerate personal transformation.

Want to learn more about Dennis McCurdy's work at McCurdy & Andrew Investments? Check out his website at https://www.mccurdyinvestments.com/

Connect with Dennis through his LinkedIn at https://www.linkedin.com/in/dennis-mccurdy-cfp-465a1bb/

Check out Dennis McCurdy's personal website at https://dennismccurdy.com/

Get a copy of Dennis McCurdy's book Unleash the Power of Connection at https://www.amazon.com/Unleash-Power-Connection-accountability-procrastinating/dp/097988635X

Transcripts

Scott Ritzheimer:

Hello, hello, and welcome, welcome once again

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to the Start, Scale, and Succeed podcast-the only podcast that

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grows with you through all seven levels of your journey as a

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founder. I'm your host Scott Ritzheimer, and too many

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founders think that grinding alone is a necessary part of

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building a business or a nonprofit, especially those of

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you in the startup entrepreneur stage, trying to succeed as a

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solopreneur, the challenge though is without anyone

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watching, very few of us does our very best, especially over

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the long haul, which leaves so many of our best ideas to gather

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dust in what my guest calls the Valley of Dead Dreams. Doesn't

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that sound wonderful? We'll talk about what that is and how to

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avoid it here in just a bit. But my guest has built a system for

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himself and spent over a decade teaching others to do the same.

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With us here today is Dennis McCurdy, who transformed his

Scott Ritzheimer:

life from graduating near the bottom of his high school class

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and sleeping on an office couch to achieving seven-figure net

Scott Ritzheimer:

worth. Following his military service, he built eight

Scott Ritzheimer:

businesses, managed 29 properties, authored four books,

Scott Ritzheimer:

and led mastermind groups for over a decade. He teaches that

Scott Ritzheimer:

mindset, accountability, and strong relationships drive true

Scott Ritzheimer:

achievement. He's the author of the book "Unleash the Power of

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Connection, and he actively runs personal development workshops

Scott Ritzheimer:

to help others reframe their failures into fuel for growth.

Scott Ritzheimer:

He consistently proves that strong network connections and

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daily discipline directly accelerate personal

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transformation. Andy's here with us today, Dennis. Welcome to the

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show. Glad you're here. I love I love me a Harvard Business

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Review stat, and and you you give us one about a study. I'll

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let you set this up for us. But what is it that that we can

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learn from this study, and how does it apply to that founder

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that's that's trying to succeed in that solopreneur stage?

Unknown:

We're talking about the we all do better when someone's

Unknown:

watching. We are yes, which is true. I mean, I just was telling

Unknown:

somebody the other day that it doesn't even have to be

Unknown:

somebody. Sometimes just a picture of somebody can, you

Unknown:

know, can cause us to to focus more, to be more accountable.

Unknown:

You know, the whole thing is, and I think that's the big

thing:

is we're not meant to do this alone. And we say that I

thing:

say that in the book. You need to really reach out to people,

thing:

be connected. Again, accountability is one of the

thing:

most important things that we can have. I always tell people,

thing:

I don't like to be pushed, but I love the results, and and we you

thing:

know we need that kind of thing. I mean, unfortunately, probably

thing:

we all need a drill instructor in our life, but we don't have

thing:

one. And and I was raised by a drill instructor, so I know how

thing:

that can go. But

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so it's a fascinating dynamic because the

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folks who go out and start their own thing tend to be more

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comfortable with doing their own thing than a lot of people, and

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and the the flip side of that, maybe the negative for or for

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better or worse, I guess, is a tendency to do our own thing,

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our own way, at our own time, on our own terms, all by ourselves.

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How do how do you help folks? Because there's a tension there

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of having that accountability, having folks that are in your

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corner and care about you, but how do we keep at bay that that

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resistance to push back, that that that rebel spirit that may

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serve us in other ways, but doesn't necessarily serve us

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well here?

Unknown:

I think that we have to understand that you know

Unknown:

basically it's accepting it's for your own good. You know, I

Unknown:

mean, because you're right, we're very independent. I always

Unknown:

tell people the best thing about being self-employed is being

Unknown:

self-employed. The worst thing about being self-employed is

Unknown:

being self-employed, because there's just nobody to to push

Unknown:

you. You know, except when you're fire a customer fires you

Unknown:

or something, which is the worst thing you want to have happen.

Unknown:

So, you know, having you know, I've had a lot of mentors in my

Unknown:

life. I've had accountability partners, and and coaches and

Unknown:

consultants I've hired. I'm actually part of a national

Unknown:

mastermind group now with about 50 other insurance agency

Unknown:

owners, and it's good to be able to have that and hear other

Unknown:

people's stories to be able to get out, get out of your own

Unknown:

way. That's our biggest our biggest problem for most people

Unknown:

in the world. Just getting out of our own way, and and we can

Unknown:

be stubborn. Plus, it's nice, you know, being the boss

Unknown:

sometimes.

Scott Ritzheimer:

Yeah, yeah. So the way that we're not going to

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go solve for this problem is to go get a boss somewhere else,

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right? That's that's that's out of the equation, at least for

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these folks. Might be right for some folks, but let's let's just

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rule that out for the the sake of the conversation. So we're

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not going to go get a boss from somebody somewhere else. Even if

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you hire an employee or two, you're their boss, and so having

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someone there might help a little bit. But it's not quite

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the same. We're not necessarily talking about going and getting

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a business partner and giving up equity in your business. These

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are all like real complicated, can work in some situations, but

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that's that's not the solution that that you've proposed here

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in the book. What

Unknown:

Having your own gang? We talked about that earlier. I

Unknown:

mean, I'm a big believer in mastermind groups. Again, I

Unknown:

think as an entrepreneur, solopreneur, you have to

Unknown:

understand and be open to these things if you really want to

Unknown:

grow and accelerate. I mean, just everybody. We're not all

Unknown:

one thing. We can't do all. Everybody has our quirks and

Unknown:

their quirks. Everybody has their strengths and their

Unknown:

weaknesses. So I remember once when I was talking to one of my

Unknown:

buddies in a group, we were saying he was saying, write all

Unknown:

the things down on the left side of a piece of paper that you're

Unknown:

good at. Write all the things on the right side that you're not

Unknown:

good at. You don't like. You should tear it in half and put

Unknown:

an ad in the paper for that part, because again, we're not

Unknown:

perfect. So having someone who you know again, why I like the

Unknown:

gang concept, having which means goal achieving nudging group.

Unknown:

It's having people around you that are not afraid to call you

Unknown:

on your stuff, because we all have stuff. I mean, if you think

Unknown:

you don't have stuff, you're in denial, right? And so, being

Unknown:

vulnerable enough to accept that and and accept the. I want to

Unknown:

say I don't want to say criticism, but accept the pushes

Unknown:

because, in fact, it was James Allen said in his book *As a Man

Unknown:

Thinketh* a person who doesn't shrink from self-criticism can

Unknown:

always achieve their goals, and so having people that will give

Unknown:

you that loving kick in the butt when you need it is really

Unknown:

important because

Scott Ritzheimer:

yeah, this is this is this is at least the

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first and may end up being the last. I don't know. We'll see.

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But episode where we talk about this question, I don't know that

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I'll ever ask this of anyone else. What's the difference

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between a good and a bad gang member.

Unknown:

A good and a bad gang. Well, a a good gang member shows

Unknown:

up for you, and you show up for them. A good gang member will

Unknown:

tell you the truth. You know whether you want to hear it or

Unknown:

not. You know to say, hey, wait a second, you know, let's get

Unknown:

off this. You've been on this too long. You're making these

Unknown:

excuses. You're not. You're you're lying to yourself. That's

Unknown:

what you want. I mean, you don't want to punt to people who just

Unknown:

say yes, yes, you're great, you're wonderful. That that

Unknown:

doesn't get you anywhere. I mean, nobody's perfect, and so

Unknown:

we're all trying to improve, you know, a little bit every day.

Unknown:

And so, and it's easy to deny, you know, hey, I'm, I'm, I'm,

Unknown:

this, I'm okay, I'm doing this, it's right, and somebody else

Unknown:

will go, wait a second here, you know, you're a little off track,

Unknown:

or you're, or you're letting some of your maybe negative

Unknown:

patterns, you know, filter in your sabotaging behaviors, which

Unknown:

we all have. I always liked that cartoon way back in the day by

Unknown:

this little guy called Pogo, and he said, "We've met the enemy,

Unknown:

and it's us. And so we have to realize and be open enough to

Unknown:

accept that.

Scott Ritzheimer:

What is your take on who to invite into your

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gang? Is it family members? Is it friends? Is it other business

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owners? What are some of the mistakes you see folks make

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there? I guess I would set up and say I think most people have

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a gang, whether they want to or not. Right, it's more that they

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haven't been selective in who that gang is. Would you agree?

Unknown:

I agree. I totally agree, and that's really

Unknown:

important. I mean, sometimes it just happens through osmosis.

Unknown:

They just, you know, and people just in our our natural life.

Unknown:

But having people in your family can create a whole. It's a whole

Unknown:

nother dynamic there. So in fact, I remember talking to a

Unknown:

woman who it was a husband, two daughters, and the wife in a

Unknown:

very successful restaurant. But there were always there was

Unknown:

always this stuff going on. In fact, one of them said, "Well, I

Unknown:

want to leave here and I want to go to New York City, and I want

Unknown:

to get a good job and I want to make this kind of money. And I

Unknown:

said, "Wait a second! You get six weeks off at this job. You

Unknown:

drive two miles to work, and you're the boss. What are you

Unknown:

talking about? So I had said to them, "You know, hire a coach

Unknown:

for the family. Hire a psychologist if you have

Unknown:

whatever you have to do, because this is a gold mine and you're

Unknown:

going to kill it. And they actually did, so they ended up

Unknown:

selling it and being miserable.

Scott Ritzheimer:

Oh, that's awesome. So

Unknown:

yeah, having that's important. Go ahead.

Scott Ritzheimer:

What are some of the best places to find your gang?

Unknown:

That's a tough one. It you have to just be very. I

Unknown:

mean, sometimes you can find them online through things like

Unknown:

LinkedIn. Sometimes through business groups, people you

Unknown:

know, even maybe even through customers who might know people.

Unknown:

It's there are some online mastermind groups now, which can

Unknown:

be helpful because you have facilitators who actually pay

Unknown:

and they facilitate the meetings and things, so that can be

Unknown:

helpful. It's it's a process, and and some and sometimes I

Unknown:

know in the book I talk about my friend Margot Chevers, and she

Unknown:

and I had decided to have a mastermind group, and so we

Unknown:

started meeting once a month, and other people said, "Well, I

Unknown:

want to come. I want to join party, be part of your group.

Unknown:

And they would come, and they would they would they would show

Unknown:

up. Maybe they come twice, and then they say, "Oh, I'm just too

Unknown:

busy on this. I said, "Well, we're busy, but we show up every

Unknown:

month. We commit to our goals, and we get them done. So you're

Unknown:

too busy to do that. And Margot and I met every month for seven

Unknown:

years.

Scott Ritzheimer:

Wow!

Unknown:

And so we used to. I know. I know if you read it in

Unknown:

the book, but we used to write a check to each other after each

Unknown:

meeting for 500 bucks, post dated 30 days, and if you didn't

Unknown:

do your goals, the other person got to cash the check.

Scott Ritzheimer:

Yes. Yes. I love that. I love that, and and

Scott Ritzheimer:

I I think what that taps into is how you're saying ahead of time

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is like these are people who are advocating for you, and and when

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when you look to some of the more common places, a a spouse,

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a parent, a friend of yours, they either like a friend cares

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but doesn't necessarily understand. A family member is

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probably afraid and understands, right? But when you can find

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other people that you can, to some extent, go shoulder to

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shoulder with, like the two of you did, I think that goes back

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to what you opened with of the power of peer groups. Where did

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you find that? How did you discover that?

Unknown:

Where did I find the power-the power of a group? You

Unknown:

mean, or yeah, many, many, many years ago, I was invited to a

Unknown:

men's group that was more of a not a business group, but it was

Unknown:

just basically men building intimacy with men,

Unknown:

communicating, and I discovered all of the different opinions

Unknown:

and variety you can get from that, and that's when I decided

Unknown:

to start my own mastermind group. And then also, I when I

Unknown:

was teaching my workshops back in the day, I was concerned that

Unknown:

they would they would leave the workshop, and that would be it.

Unknown:

So I said to them, anybody who attends the workshop can come to

Unknown:

a free mastermind group. We meet every month. We had here's the

Unknown:

location. This is what we're going to do. And you know, of

Unknown:

the hundreds of people that came, only maybe about a half a

Unknown:

dozen actually did it consistently, and eventually we

Unknown:

disbanded. But you know, it was like you need to have that

Unknown:

constant accountability. Every human being needs that;

Unknown:

otherwise, we'd all be perfect, right?

Scott Ritzheimer:

For sure, for sure. Dennis, there's there's so

Scott Ritzheimer:

many different questions I could ask, and in so many ways that

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you could go with this. But there, I want to make time for a

Scott Ritzheimer:

question that I ask all my guests. I'm interested to see

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what you have to say, and the the question is this: What would

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you say is the biggest secret that you wish wasn't a secret at

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all? What's that one thing you wish every founder watching or

Scott Ritzheimer:

listening today knew?

Unknown:

You don't have to do it alone. It's it's that simple.

Unknown:

You can, and if you're, if you don't want to involve, like say,

Unknown:

a gang kind of person, get yourself a coach or consultant,

Unknown:

someone that you trust enough and you have enough, like

Unknown:

enough, where you're willing to open yourself up to take that

Unknown:

advice again, because nobody's good at everything, nobody's

Unknown:

perfect at everything, and so we need to really recognize that.

Unknown:

Because if you if you can capitalize and move past your

Unknown:

weaknesses, almost anything's impossible. Impossible. It's

Unknown:

just a matter of doing that and being humble enough. I think.

Unknown:

Sometimes, which is harder when, as you get more successful,

Unknown:

sometimes.

Scott Ritzheimer:

Yeah, yeah, it really is. It can become more

Scott Ritzheimer:

and more isolating. There's some folks listening that they're

Scott Ritzheimer:

they're ready to start a gang, or or they're they're just

Scott Ritzheimer:

interested in learning more and how they can not do this alone.

Scott Ritzheimer:

Tell us a little bit about the book. Remind us of the name and

Scott Ritzheimer:

where we can get a copy of it, and then how folks can connect

Scott Ritzheimer:

with you and learn more.

Unknown:

Sure. So the name of the book is "Unleash the Power

Unknown:

of Connection, and it can be bought on Amazon or Barnes and

Unknown:

Noble or Digital Chalk or any of those any of those platforms,

Unknown:

and they can reach me at just. McCurdy.com. If they want to

Unknown:

reach out, be happy to chat with them, give them some ideas. I've

Unknown:

been involved in a lot of mastermind groups and a lot of

Unknown:

coaching and consulting from from both sides, both giving and

Unknown:

receiving. So I'm very open to. Yeah, I think you have to be

Unknown:

open to learning and being. You know, realize you're not

Unknown:

perfect.

Scott Ritzheimer:

Yeah, yeah. So true. So true. Recommend it,

Scott Ritzheimer:

especially those of you who have that feeling of being alone,

Scott Ritzheimer:

because you're the only one in your business. That's a very

Scott Ritzheimer:

real thing, but it doesn't have to be that way. And Dennis, I

Scott Ritzheimer:

love the idea, love the approach. Really enjoyed the

Scott Ritzheimer:

book, and really enjoyed this conversation. Thanks for being

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on. It was really a privilege having you here, and for those

Scott Ritzheimer:

of you watching and listening, you know your time and attention

Scott Ritzheimer:

mean the world to us. I hope you got as much out of this

Scott Ritzheimer:

conversation as I know I did, and I cannot wait to see you

Scott Ritzheimer:

next time. Take care.

Unknown:

Thanks, Scott.

Scott Ritzheimer:

Hey, everyone. Scott Ritzheimer here. Thank you

Scott Ritzheimer:

so much for listening to the Start Scale and Succeed podcast.

Scott Ritzheimer:

I hope this episode gave you exactly what you need for the

Scott Ritzheimer:

level you're in right now. If you want to discover what level

Scott Ritzheimer:

you're in, take our 10 question Founders Evolution Quiz for free

Scott Ritzheimer:

at foundersquiz.com. That's foundersquiz.com. It'll pinpoint

Scott Ritzheimer:

exactly where you are, and give you tailored tips to move

Scott Ritzheimer:

forward and reach that next level in your journey as a

Scott Ritzheimer:

founder. If you got something out of today's episode, don't

Scott Ritzheimer:

forget to subscribe, rate, or review. It helps us reach more

Scott Ritzheimer:

founders like you, and let's be honest, it means a ton to me, my

Scott Ritzheimer:

team, and all our incredible guests. So keep starting,

Scott Ritzheimer:

scaling, and succeeding, and I'll see you in the next

Scott Ritzheimer:

episode.

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