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Your Best Sales Rep Is a Ticking Time Bomb with Ben Wright (stage 4) - Ep. 410
Episode 4107th July 2026 • The Start, Scale & Succeed Podcast • Scott Ritzheimer
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In this revelatory episode, Ben Wright, Director of Stronger Sales Teams, shares why relying on one superstar sales rep can put your entire business at risk. If you're in stage 4 feeling dangerously dependent on a top performer, worried about what happens if they leave or burn out, you won't want to miss it.

You will discover:

- Why depending on a single high-performing sales rep creates massive vulnerability for your company

- How to build simple, repeatable processes so your sales engine runs without any one person

- What multi-layer customer relationships look like to protect key accounts

This episode is ideal for for Founders, Owners, and CEOs in stage 4 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

Ben Wright is a seasoned sales team builder, strategist, coach, and an avid believer that the best sales leaders must constantly sharpen their tools to maintain a competitive edge. He has built high-performing sales teams from the ground up across the corporate world, fast-growth startups, and mature businesses alike. Notably, his last venture was recognized as an Australian Growth Company award winner for two consecutive years, scaling from $0 to $40M in ARR in just over seven years. Defined by grit, Ben is a leader who truly thrives when stepping up to a challenge. Ben is a published contributor to HubSpot and LinkedIn who brings immense energy to everything he does.

Want to learn more about Ben Wright's work at COMPANY? Check out his website at http://www.strongersalesteams.com/

Connect with Ben through his LinkedIn at https://www.linkedin.com/in/coachbenwright/

Transcripts

Scott Ritzheimer:

Hello, hello, and welcome, welcome once again

Scott Ritzheimer:

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

Scott Ritzheimer:

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

Scott Ritzheimer:

founder. I'm your host, Scott Retheimer, and today's topic is

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for those of you who either want, or maybe even worse,

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already have an amazing sales rep. Sounds like such a problem,

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doesn't it, because it just might not be all that it's

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cracked up to be, and most founders don't even realize how

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exposed they are until that top rep leaves, burns out, or

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something else happens, and here to help us out, here to not only

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figure out what's wrong with having a great sales rep, or

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what could be wrong with it, but to also find a better way

Scott Ritzheimer:

forward is the one and only Ben Wright, who is a seasoned sales

Scott Ritzheimer:

team builder, strategist, coach, and an avid believer that the

Scott Ritzheimer:

best sales leaders must constantly sharpen their tools

Scott Ritzheimer:

to maintain a competitive edge. He's built high-performing sales

Scott Ritzheimer:

teams from the ground up across the corporate world, fast with

Scott Ritzheimer:

startups and mature businesses alike. Notably, his last venture

Scott Ritzheimer:

was recognized as an Australian growth company award winner for

Scott Ritzheimer:

two consecutive years, scaling from $0 to 40 million in annual

Scott Ritzheimer:

receiving or annual recurring revenue in just over seven

Scott Ritzheimer:

years. Defined by grit, Ben is a leader who truly thrives when

Scott Ritzheimer:

stepping up to a challenge, Ben's a published contributor to

Scott Ritzheimer:

HubSpot and LinkedIn, who brings immense energy to everything

Scott Ritzheimer:

that he does. He's here with us today. Ben, welcome to the show.

Scott Ritzheimer:

I'm really excited about this conversation, because, as I

Scott Ritzheimer:

mentioned coming in, I've got several clients who are dealing

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with this very thing right now, super successful founders doing

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10 million plus a year and dangerously close to peril at

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every single moment of that, because they've got this great

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sales rep that they've written on the back of for years now,

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and they're starting to feel the cracks. What's going on here?

Scott Ritzheimer:

Why is having a great sales rep potentially such a problem?

Unknown:

Well, first of all, Scott, thanks very much for

Unknown:

having me on today. And we talk about grit in that intro and

Unknown:

problems. We've had the trifecta this morning. We have first of

Unknown:

all, we have my deep, heavy Australian accent, which I get

Unknown:

asked all the time to, 'Hey, Ben, slow down. I love your

Unknown:

accent, but it's so deep, so I'll do my best to do that

Unknown:

today. I also have one great big black eye, and for those not

Unknown:

watching on video, jump onto video on this one, because

Unknown:

you'll see a man who has a six year old daughter who has

Unknown:

managed to break his nose, displace his nose, slit his eye,

Unknown:

and give him concussion with one smooth move of a surfboard, and

Unknown:

then the third one is we had some connectivity issues jumping

Unknown:

on because we are, we are that far apart in the world, so we've

Unknown:

had a beautiful start to this morning, but from adversity

Unknown:

often comes great results. So, I'm so, thank you for having me

Unknown:

on, and certainly my job today is to try and help, particularly

Unknown:

those founders we speak about, who have one high performing

Unknown:

rep, both a blessing and a curse. We'll try and think of a

Unknown:

couple of ideas that they can have that are going to help them

Unknown:

move the dial immediately to keep their business growing, but

Unknown:

also protect them. So that's my job, I see, for the next 15

Unknown:

minutes or so with you. But if we look at a founder who has

Unknown:

managed to move their sales team from just them, right, they're

Unknown:

out there, they're carrying the bag, they're doing all the hard

Unknown:

work into having one person who's running their sales and

Unknown:

doing, let's say, in this, in this instance, a terrific job.

Unknown:

The first thing I'm going to say is, well done. To be able to

Unknown:

move from founder-led sales to a team of selling is one of the

Unknown:

most difficult steps you can have in any business. It's like

Unknown:

going from being an individual contributor in an organization,

Unknown:

to a leader of people, super difficult steps. So, the first

Unknown:

thing I'll say is, well done. The second thing I'll say is,

Unknown:

the challenge is only just beginning, because exactly as

Unknown:

you say, when we have one sales person in our team, we can

Unknown:

become really heavily reliant on them, and without the right

Unknown:

processes behind them, and that word is so important, it can, of

Unknown:

course, elicit a bit of fear into people. Process, what's

Unknown:

process? What am I going to do here? Processes get really

Unknown:

complex. Do I need to use AI? Do I need to have it written down?

Unknown:

How many people have got to be involved in the process? Right,

Unknown:

it can get that prefrontal cortex running a little bit hard

Unknown:

for people, but at the same time, process can be so simple.

Unknown:

So, without the right process, and I'm going to say the words

Unknown:

simple process behind anyone in your sales team, whether you

Unknown:

have one or 21 people, like we had in our business at the

Unknown:

height of our business, having that great process behind these

Unknown:

salespeople is just so important to be able to build that growth.

Unknown:

So we might dive into that today to give your founders and your

Unknown:

entrepreneurs some tips around how they can manage a team of

Unknown:

one or a team of two,

Scott Ritzheimer:

that's so great. I couldn't agree more on

Scott Ritzheimer:

a couple points. One, I forgot to mention this earlier, but

Scott Ritzheimer:

this is now available in both Apple Podcasts and Spotify on

Scott Ritzheimer:

video, so we've definitely got you covered, so. Everyone can

Scott Ritzheimer:

see the effects of your six year old, but yeah, in either those

Scott Ritzheimer:

platforms, jump on the video, it's a great feature in both,

Scott Ritzheimer:

but no, to the point of today's episode, I think that it's so

Scott Ritzheimer:

wonderful when you can solve for the being the only salesperson

Scott Ritzheimer:

that, like, you'll take anything, and when that anything

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happens to be a fantastic individual that can actually

Scott Ritzheimer:

like outsell what you did, which happens sometimes, like I most

Scott Ritzheimer:

founders at that level just can't think of anything better,

Scott Ritzheimer:

you know, and so I think one of the things that's so difficult

Scott Ritzheimer:

is just kind of mentally how we get stuck in this space of maybe

Scott Ritzheimer:

you can speak to this for us, but one of the challenges that I

Scott Ritzheimer:

see is it's really tough to find another one of those and to

Scott Ritzheimer:

bring them on, and so even if they try and hire out a team,

Scott Ritzheimer:

the expectations are just so outsized that that they end up

Scott Ritzheimer:

just keep falling back to this one person, and you can feel

Scott Ritzheimer:

trapped if it's all down to one person.

Unknown:

Yeah, absolutely. Agree. So, what I might do is

Unknown:

put to side, for the moment, the piece around how you can retain

Unknown:

that person. It's so critical, and no doubt you've spoken about

Unknown:

that in your podcast, but there's ways we can retain

Unknown:

people through not just salary, through through learning,

Unknown:

through cultural benefits, through flexibility, through

Unknown:

lots of different things. Here we probably won't go down those.

Unknown:

I won't go down that area today. I might look at more around what

Unknown:

do we do to protect the business, so that if that person

Unknown:

either stops performing, and I have seen many elite sales

Unknown:

people stop performing overnight for various reasons, or if that

Unknown:

person decides to leave. What you do to make sure that your

Unknown:

business doesn't go from a screaming success into one that

Unknown:

you know creates a bundle of nerves for you as the owner. And

Unknown:

I think if we're looking at this, let's take a drive, you

Unknown:

know, drive down down memory lane for me, where I've had

Unknown:

businesses which have two types of sales funnels. So the first

Unknown:

time with that high performing salesperson is a business where

Unknown:

I'd call it your job in so you're winning deal, completing

Unknown:

deal on to next deal, winning deal, completing deal on to next

Unknown:

deal. So that's very much that hunting style business versus

Unknown:

businesses where you have fewer accounts, but they're bigger and

Unknown:

they stay with you, and you provide to those accounts again

Unknown:

and again and again, and this example also works when you're,

Unknown:

when you have smaller accounts, but lots of them, but they're

Unknown:

repeat customers, and they're two very different streams of

Unknown:

sales. One requires the ability to make relationships quickly,

Unknown:

build confidence, trust, you know, show your knowledge very

Unknown:

quickly, help your customers out, and then win deals, and the

Unknown:

other one requires you to maintain and foster

Unknown:

relationships, so if we look at the situation where you are a

Unknown:

business owner and you are looking to win new deals again

Unknown:

and again and again, and you have one salesperson that's out

Unknown:

there, they're hunting, they're knocking down doors, they're

Unknown:

calling inbound leads quickly, they build those great

Unknown:

relationships, and they're closing deals. In that instance,

Unknown:

for me, where I see leaders have some reassurance that if that

Unknown:

salesperson is going to move on is where they've built a very -

Unknown:

and this is so important - a very simple process behind it,

Unknown:

and that process, in our experience, normally comes down

Unknown:

to a framework that we call the core three model, or the core

Unknown:

three framework, which is all about speed, value, and process,

Unknown:

and if we can build a very simple sales process that

Unknown:

focuses on speed to lead, so how quickly we're engaging with our

Unknown:

customers, and that's very much, and we don't have lots of time

Unknown:

to dive into this today, but it's very much around making

Unknown:

sure your energy levels in how you contact your customer match

Unknown:

theirs, so if we can build a process around speed, we can

Unknown:

build a process that has ingrained into how you contact a

Unknown:

customer, qualify your customer, get to site, complete your site

Unknown:

audit, and if it's on the phone or video, that's okay too. Very

Unknown:

similar process, right? Close out that site visit, quote,

Unknown:

follow up, win, lose, review that deal where you have a very

Unknown:

simple process in there. My experience is that it's far

Unknown:

easier to bring in sales people to then move into, or to repeat

Unknown:

that process outside of your gun, right?

Unknown:

You're one expert, but I think the piece that gets missed by

Unknown:

most entrepreneurs and most founders is that they rely on

Unknown:

that gun salesperson to do whatever they want, so what you

Unknown:

end up doing is you get their model of selling rather than the

Unknown:

business's model of selling, and that's when you're at risk,

Unknown:

because whilst you don't lose relationships when they leave

Unknown:

the business, you might lose an active pipeline, but that's

Unknown:

okay, most businesses are turning over their pipeline 10

Unknown:

to 12 times a year, so you might lose that active pipeline, and

Unknown:

okay, but you have to step in as the founder and close that and

Unknown:

work that, and you have a short sprint where you need to

Unknown:

recover, but where you've built that process into something

Unknown:

that's simple and repeatable, it's far easier to replace that

Unknown:

with a salesperson that will get the job done, so that is without

Unknown:

doubt my number one recommendation is you must

Unknown:

simplify into a simple process where you have. Hunting style

Unknown:

mentality, when we look at the second option, which is, sorry,

Unknown:

Scott, over there. Yeah, let

Scott Ritzheimer:

me, let me follow up on that, because one

Scott Ritzheimer:

of the things you say, simplify, and I think that's really,

Scott Ritzheimer:

really smart, and I really like this idea of the business's

Scott Ritzheimer:

process, not the salesperson's one of the, one of the things

Scott Ritzheimer:

I've found complicates that, and this just might be my shallow

Scott Ritzheimer:

experience. So, feel free to speak into it, but is sometimes

Scott Ritzheimer:

you just, you don't have a wealth of that same level of

Scott Ritzheimer:

performance sitting around, right? So, if one person's

Scott Ritzheimer:

bringing those all in and they do 5 million, and you bring in

Scott Ritzheimer:

another person and they do two, it feels like the end of the

Scott Ritzheimer:

world, but it's still 2 million in revenue created. How do you

Scott Ritzheimer:

know? Like, is there a, is there a simplifying of expectations?

Scott Ritzheimer:

Is there a level setting of expectations that have to come

Scott Ritzheimer:

with that process? How do they assess whether or not that $2

Scott Ritzheimer:

million performer is worth it.

Unknown:

Yeah, look, it is a great question, and without

Unknown:

doubt, such as life, that we will have different levels of

Unknown:

performance in any function in our business, operations,

Unknown:

customer service, legal, finance, whatever it may be, and

Unknown:

sometimes you do get star performers, and sometimes those

Unknown:

star performers leave, and I always see that as as an

Unknown:

opportunity to learn when we get that star performer in to make

Unknown:

our business better, but when it comes to expectations, the

Unknown:

simplest that I have in terms of whether or not you have a profit

Unknown:

generating, not a revenue generating, but a profit

Unknown:

generating salesperson, is that they are driving 10 times their

Unknown:

salary into their business. For most businesses, that's a very

Unknown:

basic benchmark. If you get someone that's going over that,

Unknown:

well, then they are over performing, and that's when how

Unknown:

you retain that person becomes really important, as well as, of

Unknown:

course, building that sales process, but if you have a

Unknown:

$200,000 a year headcount generating $2 million a year in

Unknown:

revenue for most businesses, that's a profitable sales

Unknown:

person.

Scott Ritzheimer:

Yeah, yeah, that's really helpful, and, and

Scott Ritzheimer:

I like that it, it simplifies it to what's necessary for the

Scott Ritzheimer:

organization to succeed, because oftentimes there's just a lot of

Scott Ritzheimer:

emotion in the process as a whole, and so I think it's just

Scott Ritzheimer:

a really helpful rule. So, all right, we've got the hunter,

Scott Ritzheimer:

that person's got to rapidly create those connections, and

Scott Ritzheimer:

we've got that side equation. Let's talk a little bit about

Scott Ritzheimer:

more account-based sales or recurring revenues, what happens

Scott Ritzheimer:

with the elite performer on that side of things?

Unknown:

So, when we have that elite performer who's built

Unknown:

those relationships, that's where I see founders get really

Unknown:

nervous, and I certainly had that in my business. We had a

Unknown:

team of 21 but off that 21 we had three salespeople that were

Unknown:

generating around about half our revenue, so we had 18

Unknown:

salespeople generating 50% and three salespeople generating 50%

Unknown:

Now, the good news for us was that if one of those people

Unknown:

left, we were able to farm out some of their work across those

Unknown:

18, but that's not always the case when you're running your

Unknown:

own businesses. The strongest recommendation I have here, and

Unknown:

hopefully, as leaders and founders listening, you've heard

Unknown:

this before, but it comes down to your execution of it, is

Unknown:

making sure that you have multi-layer connections across

Unknown:

those customers, and what that means is that in any business

Unknown:

that's key account driven, it's never just driven with one

Unknown:

relationship, because any single point of contact in anything in

Unknown:

this world, we have four wheels on the road. We have two legs

Unknown:

when we walk along, right? We could go on examples here

Unknown:

forever, but anytime in this world you have a single point of

Unknown:

contact. If that fails, well, then the relationship is broken.

Unknown:

So, it's really important that you, I mean, let's, and let's

Unknown:

have a look at larger accounts. If you have larger key accounts,

Unknown:

generally it's the founders of the business that will step in

Unknown:

and also have a relationship with with more than one contact

Unknown:

in that business, so we end up going from a one to one

Unknown:

connection to a symbiotic, and on video you can see my hands

Unknown:

moving in some really, really weird way here, right, but we

Unknown:

have multiple layers of connections where you have 234,

Unknown:

people in your business, or two at a bare minimum, contacting

Unknown:

234, people in your customer's business, when you have a

Unknown:

smaller business, so if you're a founder that's doing

Unknown:

transactions that are lots of $1,000 $5,000 $10,000

Unknown:

transactions, where it's really not feasible for you to also

Unknown:

have a relationship with 100 customers, well, where you then

Unknown:

have your customer service team, or your operations team, your

Unknown:

delivery teams having relationships that support your

Unknown:

key salesperson, then what we're doing then is, if that sales

Unknown:

person leaves, is we are buying ourselves time, because that's

Unknown:

the key game here. Good key accounts where you have multiple

Unknown:

relationships, where they lose one contact. If your service is

Unknown:

good and your product is good, they won't leave. However, you

Unknown:

still need to be able to replace that front-end service in a

Unknown:

reasonable amount of time, so I really like the approach around

Unknown:

multi layering and multi contacts across these customers

Unknown:

as ones that you see as an insurance policy to buy you time

Unknown:

if and when, and the answer is generally when your top

Unknown:

performing salespeople leave. It happens, it's life, it's

Unknown:

cyclical. So, there's a couple of ideas in there that can help

Unknown:

you. Start to generate some stability and stop you having

Unknown:

that moment at home when you're eating dinner and your kids are

Unknown:

around and you're not present, so we've all been there.

Scott Ritzheimer:

That's so good. Two more questions. One's

Scott Ritzheimer:

one of my favorites, and the other is a nice easy softball

Scott Ritzheimer:

for you. But the first question here is one that asks all my

Scott Ritzheimer:

guests, and it is, what is the biggest secret that you wish

Scott Ritzheimer:

wasn't a secret at all? What's that one thing you wish every

Scott Ritzheimer:

founder watching or listening today knew?

Unknown:

Yeah, so look, I've been asked this question before,

Unknown:

and I had a number of runner-ups, but I think with

Unknown:

this topic that we're talking about today, what I'd really

Unknown:

like to encourage any founder or any entrepreneur to focus on is

Unknown:

speed, so now I don't know if speed's a secret, but

Unknown:

implementation of speed is, and too often I see sales

Unknown:

businesses, even with their high-performing salespeople,

Unknown:

rely on their heads, as we've spoken about, to get deals done.

Unknown:

Where you have a process that prioritizes speed, it allows you

Unknown:

to match your energy with the customer's energy, when they're

Unknown:

inquiring, you're responding, and when someone's inquiring, at

Unknown:

that moment you have the greatest sense of curiosity, or

Unknown:

engagement, or excitement. All right, when you, when you

Unknown:

quickly get out to see that customer again, you're pairing

Unknown:

with that, right? When you're asking the right questions

Unknown:

quickly, what do you need? What are you ready to buy now? Are

Unknown:

you just looking right? What do we need to do to get this moving

Unknown:

forward? Who's involved? When do we want to do it by right? These

Unknown:

great questions, when you're asking them quickly, you have

Unknown:

engagement from the customer and you're building relationship

Unknown:

naturally. So, any anyone that's listening that is worried about

Unknown:

that, about their key one, two single sales people having too

Unknown:

much of the business on their shoulders, speed up that sales

Unknown:

process, and you'll find that you'll be able to replace those

Unknown:

people far easier if something goes wrong.

Scott Ritzheimer:

Fantastic, fantastic. I love you. I'm glad

Scott Ritzheimer:

you came back to it, because it struck me earlier, and I didn't

Scott Ritzheimer:

know if we'd get back to it. So, I love this focus on speed. I'm

Scott Ritzheimer:

sitting here thinking of all the situations where I probably

Scott Ritzheimer:

would have bought more if they were fast for me, and then I'm

Scott Ritzheimer:

thinking of all the situations that I wasn't fast enough when

Scott Ritzheimer:

someone else was interested, so I love that. Ben, folks are

Scott Ritzheimer:

listening to this, and they either find themselves in the

Scott Ritzheimer:

position we talked about with that star sales rep, but unable

Scott Ritzheimer:

to really scale beyond it, or worried that they might cave in

Scott Ritzheimer:

without it, or they're just trying to grow their sales, and

Scott Ritzheimer:

they want someone who knows what they're doing to come out

Scott Ritzheimer:

alongside and help out. Where can they find more out about the

Scott Ritzheimer:

work that you do? What resources do you have for them?

Unknown:

Thank you, Scott. I really appreciate it. So, we do,

Unknown:

on a really limited basis, we do quote audits for selected

Unknown:

podcasts, and we've agreed to do it with the Start Scale and

Unknown:

Succeed podcast. We're going to put a link up into your show

Unknown:

notes, where you can book in to have a quote audit, and that

Unknown:

quote audit, it takes a couple of minutes to do a quick quiz

Unknown:

there, and then we look at exactly where you've got some

Unknown:

holes in your quoting process, queue right risk management, or

Unknown:

your business, or the ability to grow quickly, so that'll be in

Unknown:

the show notes, and you can jump straight in if that, if you'd

Unknown:

like some help straight away, it doesn't cost anything. There's

Unknown:

no obligation. We just do it as a thank you for having us on the

Unknown:

podcast. Or, alternatively, you can jump onto our podcast, which

Unknown:

is it's called Trade Sales Made Simple. So, it's a fantastic

Unknown:

podcast. It is generally directed at trade sales, but it

Unknown:

applies to so many more businesses than that. And I'd

Unknown:

probably start when we talk about speed. I'd actually start

Unknown:

around episode 185 That is a great little 12 minutes, like

Unknown:

yours short and chunky, around speed and how you can improve

Unknown:

that in your business. So, that'd be the two ways. And

Unknown:

thank you very much for giving the opportunity to do that,

Unknown:

Scott.

Scott Ritzheimer:

Brilliant. Great. Well, Ben, thanks for

Scott Ritzheimer:

being here. Honor and privilege having you from the other side

Scott Ritzheimer:

of the world, bright and early, beat up and all, but here with

Scott Ritzheimer:

us nonetheless. We really appreciate your, your sharing

Scott Ritzheimer:

with us here this morning. And for those of you watching and

Scott Ritzheimer:

listening, you know your time and attention mean the world to

Scott Ritzheimer:

us. I hope you got as much out of this conversation as I know I

Scott Ritzheimer:

did, and I cannot wait to see you next time. Take care.

Scott Ritzheimer:

Hey everyone, Scott Ritzheimer here. Thank you so much for

Scott Ritzheimer:

listening to the Start Scale and Succeed podcast. I hope this

Scott Ritzheimer:

episode gave you exactly what you need for the level you're in

Scott Ritzheimer:

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

Scott Ritzheimer:

take our 10 question founders evolution quiz for

Scott Ritzheimer:

[email protected] 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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