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November 4, 2025 19 mins

In this engaging episode, John Whitt, Owner of BusinessWhitt, shares how to break free from the founder's trap and turn ideas into money. If you struggle with overwhelm and scaling, you won't want to miss it.

You will discover:

- How to prioritize clarity to guide your business strategy

- What team-building steps boost your growth potential

- How to use testing to validate ideas before scaling

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

John Whitt is an experienced coach and the author of Checkmate!: Translating Ideas Into Money, a book that uses chess as a metaphor for business strategy. John brings over 30 years of experience helping both corporations and small businesses shift their culture, boost results, and improve profitability. As a leadership coach and business growth strategist, he specializes in assisting founders to move from high-stress hustle to structured, values-aligned scale.

Want to learn more about John Whitt's work at BusinessWhitt? Check out his website at https://businesswhitt.com/

Grab a copy of his book Checkmate!: Winning Tactics for Translating Ideas into Money at https://www.amazon.com/Checkmate-Winning-Tactics-Translating-Ideas/dp/1947341979

You can follow John through his Facebook at https://www.facebook.com/BusinessWhitt/ and connect in LinkedIn at https://www.linkedin.com/in/coachjohnwhitt/

Mentioned in this episode:

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Scott Ritzheimer (00:00):
Hello, hello and welcome. Welcome once again
to the Start scale and succeedpodcast. It's the only podcast
that grows with you through allseven stages of your journey. As
a founder, I'm your host, ScottRitzheimer, and there's a
pattern that I see constantly,one where founders who've
finally gone full time, who arein their business, they're
generating revenue, they'redoing their thing, they've got

(00:20):
clients, and they're drowningthe salesperson, the delivery
person, the accountant, themarketer, the janitor, and
everything in between. You wakeup every morning, and the first
thing you have to do is getthrough all the admin that you
missed yesterday and the daybefore and the day before that
before the clients start, andeverything goes crazy. And so

(00:42):
what do we how do we deal withit? How do we focus to grow?
Especially because you havethese ideas, you know that
they're going to change the verynature of the game, but you just
can't seem to get to them. Andwhat's really challenging about
this stage, what makes it sobrutal, is that you're pretty
good at the stuff that you do,too. That's why folks have hired
you. But you can't keep this up.You can't keep this cycle going.

(01:06):
And so how do we shift this? Howdo we turn it around? I'd tell
you if I knew, but I havesomething better for you. I've
got the one and only John Witt,who's been doing this for 30
years. He's been helpingfounders to break this cycle,
and he's also the author of thebook, checkmate, translating
ideas into money. It's a bookthat uses chess as a metaphor
for business strategy. Johnbrings over 30 years of

(01:28):
experience helping bothcorporations and small business
owners shift their culture,boost their results and improve
profitability. As a leadershipcoach and Business Growth
strategist, he specializes inassisting founders to move from
high stress hustle tostructured, values aligned
scale, and he's here with ustoday. John, welcome to the
show. So excited to have youhere. Love the name of the book,

(01:51):
Turning ideas to money, that isthe game, isn't it. Why is that
so hard to do?

John Witt (01:56):
Well, Scott, first off, let me say thanks for
having me today. I reallyappreciate it. It's it's hard to
do because most people haven'tdone it before. If you've done
it and again, when you, when youthink about transiting ideas
into money or it's a goal,starting a business is a goal. I
want to start a business. I wantto generate revenue. You've
never done it before. I actuallyteach a program called Achieving

(02:18):
uncommon events, because gettinggoing from zero to a successful
business is not all that common.There are a lot of people that
go from zero to an unsuccessfulbusiness as opposed to
successful, and it's really it'sa system and a process, and it's
all brand new. And you'relearning a lot, really fast. And
when you're learning a lot, alot of times, you make some
mistakes, and man, you have tohave some perseverance it's a

(02:40):
discipline, and you got to keepgetting back up and getting in
the fight, because if you giveup, it's over.

Scott Ritzheimer (02:46):
Yeah, one of the things that you talk I've
heard you talk about, is thisidea of judgment mode, and it's
something that keeps us stuck,even when we have good ideas.
What is judgment mode and why isit so dangerous?

John Witt (03:02):
Well, it's a preset condition. Instead of, you know,
an open mind, it's a fixed mind.And so judgment mode shows up
when I'm working with a client,and I've worked with many of
them in this space, andsometimes this is what we have
to get through first. And I'llsay, so you want to save some

(03:22):
time, you need to get some moretime. So why don't we? Why don't
we hire a virtual assistant?Right? That's a real common
process. And they'll say, oh,no, I can't do that. I've
already tried that. It doesn'twork. Well, see, they tried it,
that's true, and it didn't work.That's true, but that doesn't
mean they did it, right? So soreally, they're kind of stuck.
And so when somebody says no orthat doesn't work, that's like
turning the light switch off. Sothen we have to say, okay, but
well, maybe, you know, there areother people that have done this

(03:45):
and had made it work. You thinkmaybe you could try it a
different way, and it could beany number of different things,
but the, you know, they'represet because they've, they've
made a decision that that won'twork, and it's, it's false
information, you know, theybasically, it's only in their
head where it doesn't work.

Scott Ritzheimer (04:01):
Right, right. Now, you've got a framework in
the book the five key attributesfor success that help to
translate ideas into money. I'mwondering if you could just kind
of briefly walk us through thoseand how someone could take that
structure and start to put it touse today.

John Witt (04:18):
Yeah, absolutely. So step number one is clarity. And
clarity is king. In the in thechess world, the queen is the
most powerful piece on theboard. In the business world,
clarity is the most powerfulpiece on the board, and it's not
clarity at the 60 or 70% level.You want to get it as high as
you possibly can get it. Youwant to know what you're trying

(04:40):
to accomplish, who you're goingto do, what there's, there's a
whole litany of things that youwant to work with. And the
second step is Team people. Andsometimes you need some people
to help you figure out theclarity, because you don't know
all that, all the answers,right? So most, most
solopreneurs, they start up,they're not a marketing expert,
so they probably should bringsomebody from marketing onto
their team to help them. And.Are the marketing type
questions, right? So we haveclarity, and again, super

(05:04):
detailed. Bring the marketingteam, bring the person on board,
and then we get into testing andvalidation. And that's typically
the step that gets skippedfirst, right? Let's, so let's,
let's spend a little money. AndI know it's tough when you're
getting started yoursolopreneur, you're not looking
at a lot of money left over. Butlet's spend a little money and
make sure money and make surethat we're going to get the

(05:24):
results that we want. And basedon those responses, we can go
back and we can make somechanges, or we can go forward
and build a plan to launch ourproduct, or idea, our business,
our service. So the fourth stepis plan, and it's a strategic
plan. It's not just, you know,let's do X, Y and Z things.
You're really what are thethings are most important to do?
When to do it, who needs to doit? So your team is going to

(05:46):
change often, very frequently,through the process. And then
the last step is, is absolutelycritical, and that's a change
management system, because youdon't get to decide what comes
in the door tomorrow, right?Adversity shows up. You don't
get to decide when it shows up.You get to decide how you want
to respond, but if you're notpaying attention, then you don't
notice the change in the firstplace. That means you can't

(06:08):
respond and you end off, offcourse and so frequently,
especially with a business,especially when you get started,
you need to have a weekly changemanagement cadence in the
manufacturing world that I grewup in way back when, you know,
we're making big products a bigmanufacturing facility. And so
there'd be lots of people thatsay, Well, I wish it would do
this, or I wish it'd do that.Sales guys came in and said,

(06:31):
yeah, they wanted to change theproduct because the consumer
wants something a little bitdifferent. But they couldn't
just willy nilly changeeverything. So they'd have a
change control board where, youknow, whoever was looking for
the idea had to fill out all theinformation and go to the board,
and then they would, you know,decide whether they wanted to
accept that or not. I'm notsaying that you need to change
control board as a solopreneur,but a system and a process that

(06:53):
reviews what you're doing, whereyou're going, on a frequency
basis, so that you don't end upoff course. Yeah, those are the
five steps.

Scott Ritzheimer (07:01):
As folks hear that, there's kind of this
visceral reaction to that's fivesteps that I don't have time
for. So how do you startspinning that, that snowball, if
you will, in the rightdirection? Where can you use
these five steps to actuallycreate time to do the five steps
right?

John Witt (07:20):
Well, okay, so create time. That's the first
objective. And for many of thesesolopreneurs, that is, without a
doubt, the first objective, andthat's what I try to help them
do, because that's where theyget a little breath, that's
where they can reduce a littlestress. But we'll say, Okay,
well, let's bring on anassistant. Let's bring on a
virtual assistant, or let's findsomebody that we can delegate

(07:41):
these things to. Well, a, theymay not know how to do that, so
there's some training andcoaching in that space. Or B,
they're like, I can't affordthat. So okay, well, then, then
we got to figure out, how do weget more money into the system?
And you do a couple things, youcan increase your sales
conversion rate, right? Getbetter at sales, but that just
means you have to sell more andthat. So it takes more time to

(08:02):
sell more. That's not going tobe as effective. The most
effective solution that I'vefound over 15 years is raise
your prices. Raise your pricesso that you can afford to hire
an assistant. Now, most peoplesay, Well, I can't do that. You
know, my competitors. Andthey'll give you some story. And
it's like, you know, here's thething, there are seven

(08:25):
attributes. No, what is it? It'smoney is the seventh attribute
in the buying decision. So thereare six other attributes that
are more important than moneywhen it comes to making a buying
decision. We want to sell onvalue, we want to sell on
convenience. We want to sell ona lot of other things besides
price. Because we all makedecisions to buy a better
quality product or bettersystem. We don't naturally run

(08:49):
to the cheapest thing. We knowbetter in many ways. Yeah, so
let's figure out how to raiseyour prices. Now. There's a
process for doing that. I don'tthink you could just, like, flip
a switch and double your rates,but there is, you know, you're
letting your customers know.You're letting the marketplace
know. It's a it's a message. Butyou know, if you could raise
your prices by 10 or 15% or 20%that probably pays for an
assistant. Now you got 20 hoursthat you can spend some more
time doing something else, andall of a sudden, now we're we

(09:13):
got the snowball going in adifferent direction.

Scott Ritzheimer (09:15):
Yeah, I love that. I love that the time value
of money is such a big deal. Wassuch a clever thing, because
most folks, especially in likeprofessional services, are
charging too little, especiallyfor the amount of time that
they're spending doing the workthat they're doing this. Yeah,
what a great strategy there.There's another thing that comes

(09:36):
up, so let's say we've done it.Let's say we've got a little bit
of time, we've got an idea thatwe're ready to execute on, but
just saying we want to do it,and actually going out and doing
it are a couple differentthings, right? And and so
there's these stages tolearning, and you've cited the
four different stages tolearning. But how do you get

(09:56):
through that stage when yourealize you have no. Idea what
you're doing.

John Witt (10:00):
Yeah. Okay, so stage one is what I think it about.
This is unconsciousincompetence. Unconscious. I'm
not aware I'm incompetent. Idon't even know what I'm unaware
about. And so what owners haveto do founders is they have to
put themselves in positions towhere they can get exposed to
net new information, net newideas, net new concepts, on a

(10:22):
frequency basis. So that's not40 hours a week. Maybe that's a
couple hours a week. Maybeyou're at a conference, maybe
you're here. Maybe there's a lotof places where you can get
exposed to differentinformation, different
information, and depending onwhat your idea is and what your
service is, maybe there's anassociation, maybe there's a
trade show. Maybe there's acouple different ways you could
do it, but you have to investthat time, or else you'll never

(10:45):
get the direction, the guidancethat you're looking for. And
you're going to get exposed tohundreds of things. That doesn't
mean you need to do 100 things,right? Once you're exposed, now
you can make a decision, oh, outof those 100 things, I think
this one's interesting, and nowit's in your control. So you
could decide whether you want togo do it, but you have to put
yourself in stuff. You know? Thegreat example is AI, right? So

(11:06):
AI is just killing everybodyright now, and it's been a
couple years, right? There werea lot of businesses that didn't,
weren't aware of the AI. Call itrevolution, until the last six
months, and they're behind thecurve. However, if you had put
yourself in a situation whereyou could be with people, learn
from technologists, you wouldhave found out about a lot

(11:29):
sooner, and you would havestarted to figure out, hey, how
does this fit into my businesssooner.

Scott Ritzheimer (11:34):
Right? Right? That's really important. I've
actually found that somethingthat folks one of the reasons
why it's so underdeveloped andunderutilized at this stage is
because we missed the need forit in the previous stage.
Everyone's in such a rush to getout there, start their business,
do the thing, hang the shingle,you know, bring in the revenue

(11:54):
that they don't take the time toset up that learning
environment, and they pay for itin the long run. Love the way
that you brought that, broughtthat back into the equation
here, because it's so easy tomiss. But I've got a question
that I'm going to get to in justa moment. But one thing I want
to do before we get there is youtalk about this idea of a
founder's trap, and our ourlisteners who, especially those

(12:21):
who tune into the show regularare overwhelmingly founders, and
this is something that I mean weall faced at some point in time.
So tell us, what is thefounder's trap? How do we know
if we're in it, and what do wedo to get out?

John Witt (12:37):
So the founders trap is a wonderful place to be, but
it also keeps you stuck. Meansthat you've found a niche, that
you've got a way to make money.It's consistent, it's
sustainable. Maybe you have asmall team, and you're able to
manage all of that yourself, andyou've got a consistent revenue
stream coming in. And somepeople, some founders, just say,

(12:58):
hey, look, this is fine. This isall I want. But some people want
something more than that. Well,now the question is, how do I
scale? Right? So how do I andthere's two ways to scale. You
can scale with technology andyou can scale with people, and
generally you're scaling withboth. But now let's say you have
a team of five, and you can kindof watch over them on a frequent
basis. You know what they'redoing. You can correct them,
etc, etc. But what happens ifyou want to go to a team of 20

(13:21):
you? I mean, you're not gonna beable to look over their shoulder
and watch, right? So now youhave to, you have to bring in
some leaders, right? And so nowyou have to learn to lead, to
lead leaders. So when you wantto scale, and when you bring
that extra people in, you'regoing to have to bring in
additional processes. You'regoing to have to be able to
teach them and train them andhelp them grow to the next
level. And so it's reallysystems and processes that are
associated with people andtechnology that allow us to

(13:42):
scale beyond that small foundersspace and like, say it's only a
trap because you're stuck thereuntil you do something else.

Scott Ritzheimer (13:50):
Yeah, John, there's a question that I ask
all my guests, and I'minterested to see what you have
to say. And the question isthis, what would you say is the
biggest secret that you wishwasn't a secret at all. What's
that one thing you wisheverybody watching and listening
today knew?

John Witt (14:05):
Well, you know, it's a secret because most people
don't know it, but that doesn'tmean nobody knows it. And I
think it's a two part secret.The first one is generosity.
Generosity goes a long way inmany, many ways. I mean, it
covers a lot of errors. Itcovers a lot of mistakes. Covers
a lot of whoops, the idea is tobe generous with your time and
your talent, and I would sayyour treasure, and that will

(14:28):
come back to you and yourbusiness in the long run.
Generosity always, always,always delivers better long term
results. And the second one thatkind of goes along with that,
and this is where people gettangled up. You know, if they
have an employee that comes inand has an issue or a problem or
a grudge, or, you know, wants tochange something, the owner
feels like they have to respondright away. And I wish everybody

(14:51):
would learn the art of thepause, which is to pause and
say, Hey, listen, I hear you. Iunderstand. We need to have a
conversation about. About this,but now's not the right time. I
want to give it the time itdeserves. Let's set some time
for this afternoon, or let meget back to you with a better
time, and so that stops you fromspontaneously saying something

(15:11):
inaccurate or wrong orinflammatory. You know, it all
happens, right? If you have thatpause, that little pause, then,
then you have the time to thinkthrough what's the right
response. There's a little bitof time between stimulus and
response. The better you usethat time, the better results
you're going to have.

Scott Ritzheimer (15:28):
So true. It's so true. John, there's some
folks listening, and they wantto know more. How can they find
out more about the work that youdo? And where can I connect you
with you or get a copy of yourbook?

John Witt (15:40):
Well, the books on Amazon. It's called checkmate,
translating ideas into money.And if you search amazon.com,
forward slash author, forwardslash, John Witt, you'll go
right to the page. My website isbusiness wit it's a play on my
last name, businesswit.com sowww.businesswit.com there are
places where you can see all thedifferent tools and strategies

(16:02):
and things that we have. There'sa lot of, I would say, free
stuff there too, and thenthere's certainly a Contact Us
space. So if you want to spendspend some time and have a
conversation, you can certainlydo that. I'd be happy to do
that.

Scott Ritzheimer (16:15):
Fantastic, fantastic. Well, John, thanks
for being on the show today.Really was a privilege and honor
having you here. I reallyenjoyed this conversation, and
for those of you watching andlistening, you know your time
and attention mean the world tous, I hope you got as much out
of this episode as I know I did,and I cannot wait to see you
next time. Take care.
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