July 28, 2025 • 8 mins
What happens when leaders stop pretending and start leading with vulnerability?
In this episode of Leadership Levers, Tucker Graves, CEO and co-founder of Pineapple Academy, shares how his content training company unexpectedly pivoted into the world of SaaS - and the leadership lessons that came with it.
With roots in a multi-generational family business, Tucker brings a grounded perspective on culture, growth, and people. When faced with the challenge of running a company they weren’t fully equipped to lead, Tucker and his co-founder didn’t fake expertise - they asked for help.
That simple act of vulnerability became a cultural foundation, transforming how they built the team and tackled growth.
Tucker walks through:
- The real impact of process gaps when scaling a company
- How embracing vulnerability helped align their team and culture
- Why honesty builds trust faster than pretending to have all the answers
- The performance formula that guides his decisions - investments come from growth, and growth comes from people.
For leaders navigating unfamiliar terrain or high-impact growth, this episode is a reminder that admitting what you don’t know might be your greatest leadership strength.
We'd love your feedback on how we can improve - send us a Text!!
Seeking to align your culture, boost performance & impact your bottom line? Let’s chat—no sales, just real talk about your challenges. Not ready? Join our PL3 Community for free insights & connections.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
William Gladhart (00:00):
Welcome to the Leadership Levers Podcast.
I'm your host, Will Gladheart,CMO at the Culture Think Tank.
At the Culture Think Tank, weempower leaders with metrics
that strengthen culture, driveperformance and return.
We're here today to learn aboutthe actions leaders have taken
to address organizational change.
(00:21):
Today, our guest is TuckerGraves, CEO and co-founder of
Pineapple Academy.
Thanks for taking the time tojoin us.
Thanks for having me.
We'll begin by having you sharewith our audience a bit about
yourself, your background andyour organization.
Tucker Graves (00:39):
Sure, my name is Tucker Graves.
I'm the CEO of PineappleAcademy.
This is my fifth startup.
I guess I've earned thedescription of a serial
entrepreneur.
I guess there's other worsethings to be called in the world
of cereal, right, but I'm athird generation entrepreneur.
As far as I know, my grandfatherstarted a protein distribution
or manufacturing distributioncompany in Northwest Missouri,
(01:02):
predominantly focused more onkind of center of the plate,
meat items and things like that.
Essentially, what he did wellis he outsourced the butcher
from the grocery store.
My dad took the idea from mygrandfather and said hey, hey,
dad, why don't we sell thepeople who are already
delivering these products tomore stuff?
And he started down the roadwith things like frozen French
fries and things that would workin the trucks that he had that
supported those products.
And my dad ended up becoming apretty large family-owned food
(01:25):
distribution company that hesold a couple of years ago.
And then, of course, I think Iwas born into this food industry
, so most of my companies havehad some parallel, although this
one, pineapple Academy, whichis focused on frontline training
and really in the hospitalityand healthcare world, has
started in food but has evolvednow beyond that too.
Hopefully that sheds a littlelight on the background.
William Gladhart (01:46):
Yeah, absolutely.
We'll be discussing threequestions today as a warmup to
our conversation.
Can you share why you believe ahealthy culture is critical?
Tucker Graves (01:54):
Yeah, well, I think at the end of the day, the
healthy culture, if you will,of a company is really the life
kind of the lifeline of thecompany, and it speaks to one of
the metrics we should all lookat and measure, because it's the
baseline and the foundation.
A company really doesn't existwithout the people, and so
company is just a shell wherepeople all work.
In my mind, if the culture ishealthy, the company is healthy.
(02:16):
There was a great consultantthat I had he's one of our
advisors, and we were in theprocess of raising money and he
said it's really a simpleformula.
He said if you want to raisemoney, well then you have to
have growth.
And they call traction in ourworld right.
And he said and that's actuallya very simple next step,
because in order to havetraction, you have to have the
right people.
And he said so the formula issimple Investments come from
(02:40):
growth, which come from people,and so if you kind of think
about it, you just keep goingdown.
And so I remember my dad askingme one day.
He said if you could pick oneperson to hire that you think
would impact your company themost, who would it be?
And I said somebody in theworld that helped create the
best environment for people,because I believe that that
would then end up resulting inthe best performing company, if
I was the best place to work.
William Gladhart (03:01):
Yeah, I think that's really wise advice,
especially from someone who'sbeen in your industry a lot of
years but also has startedmultiple companies.
We hear over and over fromleaders right people, right
seats, right roles and also theclarity around the role and how
they're impacting theorganization is absolutely
critical.
It's been our experience thatleaders tend to struggle in
(03:23):
three key areas people, processor profits.
In your role as a leader, couldyou identify which one of these
three areas represented acultural challenge in your
organization or one of theorganizations that you started?
Tucker Graves (03:36):
Sure, I think it's interesting because of
those three.
I think, as you just said, itcan kind of change throughout
your career path.
I think we can probably say weprobably struggle at different
points with different things.
I would say my current one withPineapple Academy initially was
process.
My co-founder, greg, and I,like I just mentioned, we're
food guys and so food guys knowfood things.
(03:56):
And so we started out as acompany that created content for
the food industry and we knewthe information but we didn't
know how to package it or fancywords like the instructional
design.
And luckily Greg had been ateacher he was a chef instructor
at a university, so that gaveus a little bit of background.
But I would say that the processof how to run which we became a
(04:18):
software company because we hadput our content on a learning
management system and a bighealth system came along and
said hey, love the content,can't use your software.
Is there a way to somehow getyour content in our system?
And so we called an old friendwho had helped me with previous
companies.
We had to figure out a way tostream it and protect our
intellectual property andsupport the subscription model.
(04:39):
When all that came about and weended up pulling it off.
Greg and I were kind of lookingaround, we're laughing and
we're like holy cow.
We're a software company andwhen it came to the operations
of a software company, we didn'tknow what we were doing.
William Gladhart (04:50):
I would say process for sure.
Yeah, well, obviously theprocess element trickled into
people and profits and growth,because they're usually all
connected.
I think it's interesting thatyou not only made the pivot from
that full instructional totraining and to software.
That's a big shift.
Was there any specificchallenge that negatively
(05:11):
impacted the organization,either through growth or that
process piece?
Tucker Graves (05:16):
Oh for sure, you know, as I mentioned, the very
fact that we didn't know what wewere doing, I think that was
the biggest impact to thecompany, the culture of the
company, the people we werehiring.
We just knew what we knew andwe've run into that in our jobs
in the past where, you know,greg kind of jokingly refers
sometimes to folks in the foodservice industry, especially
when it's not their corebusiness, like a hospital, right
(05:36):
, they're in the care businessand how does somebody know how
to manage the food serviceoperations when it's not the
core business?
And so it's this idea of theblind leading the blind leading
the blind, and I think the wayto turn that around first is to
admit it, because how manypeople have we worked for in our
lives that kind of fake it tillthey make it when they should
just be honest?
I think the key here is justthe first step to this whole
(05:59):
thing is just be honest, and sous not knowing impact our growth
, that impacted our culture.
We weren't hiring necessarilyprobably the right people, but I
think the first step towardswriting it was just admitting it
and being honest about it.
William Gladhart (06:12):
Yeah, I really appreciate that answer.
Yeah, I think it's a.
It's a challenge and strugglefor leaders to.
We hear all the time in thehigh growth industry fake it
till you make it.
I'm like, well, yeah, that'sfine, but what happens when you
actually have to put up or shutup?
And that becomes a wholedifferent story and I appreciate
(06:33):
that honesty.
But I think that honesty aboutwhere the company is at really
bleeds over into the culture andthe performance of the
organization as well.
Is there one thing that you'veidentified or that you would
share with other leaders thathas kind of helped you on your
leadership journey?
Tucker Graves (06:50):
Sure, I think the most important word is
vulnerability.
I think going back to admittingwe didn't know what we were
doing, the ability to be honestabout it.
But I think the idea offlipping the narrative that
being vulnerable and asking forhelp is not a weakness, it's a
sign of strength, and that Ithink that's probably the most
important thing for any leaderis number one.
I'm always continuing to learnmy entire life.
(07:11):
I'm a lifelong learner.
All my friends are, my partneris.
I've learned more in the lastfive years than I've ever
learned in my life, probably.
And the first step, after justbeing honest that we didn't know
what we were doing, is beinghonest about the fact that we
needed help.
And so every time we hit a wallwhether it's in business
operations or people orprofitability or anything, it's
(07:31):
around this vulnerability andinstilling that in the culture
too, and telling the team to say, hey, don't come in and tell us
, like we said, don't fake it,just be honest and be vulnerable
that you need help.
And that's how honestly, that'show Greg and I have gotten out
of every situation is justsaying hey, we just need help
and not being afraid to ask forit.
So I think it's the mostimportant underlying thing.
(07:51):
Obviously, there's things likeempathy and all those things
that matter, but when we'retalking about how to right the
situation for us with process,it was about being vulnerable to
getting help.
William Gladhart (08:01):
I like that, Tucker.
I've enjoyed having you on ourLeadership Lovers podcast.
Thank you again for yourinsights.
Tucker Graves (08:07):
Absolutely Thanks for having me.
William Gladhart (08:11):
Thank you for joining us on the Leadership
Levers podcast.
Find all our Leadership Loversepisodes on the Culture Think
Tank website at www.
theculturethinktank.
com or listen on your favoritestreaming platform.
We'd love to hear from youabout the challenges you have
faced as a leader.
Tune in weekly as we inviteleaders to share their
(08:35):
experiences in strengtheningculture and performance, one
action at a time.
Welcome to the Leadership Levers Podcast.
I'm your host, Will Gladheart,CMO at the Culture Think Tank.
At the Culture Think Tank, weempower leaders with metrics
that strengthen culture, driveperformance and return.
We're here today to learn aboutthe actions leaders have taken
to address organizational change.
(00:21):
Today, our guest is TuckerGraves, CEO and co-founder of
Pineapple Academy.
Thanks for taking the time tojoin us.
Thanks for having me.
We'll begin by having you sharewith our audience a bit about
yourself, your background andyour organization.
Tucker Graves (00:39):
Sure, my name is Tucker Graves.
I'm the CEO of PineappleAcademy.
This is my fifth startup.
I guess I've earned thedescription of a serial
entrepreneur.
I guess there's other worsethings to be called in the world
of cereal, right, but I'm athird generation entrepreneur.
As far as I know, my grandfatherstarted a protein distribution
or manufacturing distributioncompany in Northwest Missouri,
(01:02):
predominantly focused more onkind of center of the plate,
meat items and things like that.
Essentially, what he did wellis he outsourced the butcher
from the grocery store.
My dad took the idea from mygrandfather and said hey, hey,
dad, why don't we sell thepeople who are already
delivering these products tomore stuff?
And he started down the roadwith things like frozen French
fries and things that would workin the trucks that he had that
supported those products.
And my dad ended up becoming apretty large family-owned food
(01:25):
distribution company that hesold a couple of years ago.
And then, of course, I think Iwas born into this food industry
, so most of my companies havehad some parallel, although this
one, pineapple Academy, whichis focused on frontline training
and really in the hospitalityand healthcare world, has
started in food but has evolvednow beyond that too.
Hopefully that sheds a littlelight on the background.
William Gladhart (01:46):
Yeah, absolutely.
We'll be discussing threequestions today as a warmup to
our conversation.
Can you share why you believe ahealthy culture is critical?
Tucker Graves (01:54):
Yeah, well, I think at the end of the day, the
healthy culture, if you will,of a company is really the life
kind of the lifeline of thecompany, and it speaks to one of
the metrics we should all lookat and measure, because it's the
baseline and the foundation.
A company really doesn't existwithout the people, and so
company is just a shell wherepeople all work.
In my mind, if the culture ishealthy, the company is healthy.
(02:16):
There was a great consultantthat I had he's one of our
advisors, and we were in theprocess of raising money and he
said it's really a simpleformula.
He said if you want to raisemoney, well then you have to
have growth.
And they call traction in ourworld right.
And he said and that's actuallya very simple next step,
because in order to havetraction, you have to have the
right people.
And he said so the formula issimple Investments come from
(02:40):
growth, which come from people,and so if you kind of think
about it, you just keep goingdown.
And so I remember my dad askingme one day.
He said if you could pick oneperson to hire that you think
would impact your company themost, who would it be?
And I said somebody in theworld that helped create the
best environment for people,because I believe that that
would then end up resulting inthe best performing company, if
I was the best place to work.
William Gladhart (03:01):
Yeah, I think that's really wise advice,
especially from someone who'sbeen in your industry a lot of
years but also has startedmultiple companies.
We hear over and over fromleaders right people, right
seats, right roles and also theclarity around the role and how
they're impacting theorganization is absolutely
critical.
It's been our experience thatleaders tend to struggle in
(03:23):
three key areas people, processor profits.
In your role as a leader, couldyou identify which one of these
three areas represented acultural challenge in your
organization or one of theorganizations that you started?
Tucker Graves (03:36):
Sure, I think it's interesting because of
those three.
I think, as you just said, itcan kind of change throughout
your career path.
I think we can probably say weprobably struggle at different
points with different things.
I would say my current one withPineapple Academy initially was
process.
My co-founder, greg, and I,like I just mentioned, we're
food guys and so food guys knowfood things.
(03:56):
And so we started out as acompany that created content for
the food industry and we knewthe information but we didn't
know how to package it or fancywords like the instructional
design.
And luckily Greg had been ateacher he was a chef instructor
at a university, so that gaveus a little bit of background.
But I would say that the processof how to run which we became a
(04:18):
software company because we hadput our content on a learning
management system and a bighealth system came along and
said hey, love the content,can't use your software.
Is there a way to somehow getyour content in our system?
And so we called an old friendwho had helped me with previous
companies.
We had to figure out a way tostream it and protect our
intellectual property andsupport the subscription model.
(04:39):
When all that came about and weended up pulling it off.
Greg and I were kind of lookingaround, we're laughing and
we're like holy cow.
We're a software company andwhen it came to the operations
of a software company, we didn'tknow what we were doing.
William Gladhart (04:50):
I would say process for sure.
Yeah, well, obviously theprocess element trickled into
people and profits and growth,because they're usually all
connected.
I think it's interesting thatyou not only made the pivot from
that full instructional totraining and to software.
That's a big shift.
Was there any specificchallenge that negatively
(05:11):
impacted the organization,either through growth or that
process piece?
Tucker Graves (05:16):
Oh for sure, you know, as I mentioned, the very
fact that we didn't know what wewere doing, I think that was
the biggest impact to thecompany, the culture of the
company, the people we werehiring.
We just knew what we knew andwe've run into that in our jobs
in the past where, you know,greg kind of jokingly refers
sometimes to folks in the foodservice industry, especially
when it's not their corebusiness, like a hospital, right
(05:36):
, they're in the care businessand how does somebody know how
to manage the food serviceoperations when it's not the
core business?
And so it's this idea of theblind leading the blind leading
the blind, and I think the wayto turn that around first is to
admit it, because how manypeople have we worked for in our
lives that kind of fake it tillthey make it when they should
just be honest?
I think the key here is justthe first step to this whole
(05:59):
thing is just be honest, and sous not knowing impact our growth
, that impacted our culture.
We weren't hiring necessarilyprobably the right people, but I
think the first step towardswriting it was just admitting it
and being honest about it.
William Gladhart (06:12):
Yeah, I really appreciate that answer.
Yeah, I think it's a.
It's a challenge and strugglefor leaders to.
We hear all the time in thehigh growth industry fake it
till you make it.
I'm like, well, yeah, that'sfine, but what happens when you
actually have to put up or shutup?
And that becomes a wholedifferent story and I appreciate
(06:33):
that honesty.
But I think that honesty aboutwhere the company is at really
bleeds over into the culture andthe performance of the
organization as well.
Is there one thing that you'veidentified or that you would
share with other leaders thathas kind of helped you on your
leadership journey?
Tucker Graves (06:50):
Sure, I think the most important word is
vulnerability.
I think going back to admittingwe didn't know what we were
doing, the ability to be honestabout it.
But I think the idea offlipping the narrative that
being vulnerable and asking forhelp is not a weakness, it's a
sign of strength, and that Ithink that's probably the most
important thing for any leaderis number one.
I'm always continuing to learnmy entire life.
(07:11):
I'm a lifelong learner.
All my friends are, my partneris.
I've learned more in the lastfive years than I've ever
learned in my life, probably.
And the first step, after justbeing honest that we didn't know
what we were doing, is beinghonest about the fact that we
needed help.
And so every time we hit a wallwhether it's in business
operations or people orprofitability or anything, it's
(07:31):
around this vulnerability andinstilling that in the culture
too, and telling the team to say, hey, don't come in and tell us
, like we said, don't fake it,just be honest and be vulnerable
that you need help.
And that's how honestly, that'show Greg and I have gotten out
of every situation is justsaying hey, we just need help
and not being afraid to ask forit.
So I think it's the mostimportant underlying thing.
(07:51):
Obviously, there's things likeempathy and all those things
that matter, but when we'retalking about how to right the
situation for us with process,it was about being vulnerable to
getting help.
William Gladhart (08:01):
I like that, Tucker.
I've enjoyed having you on ourLeadership Lovers podcast.
Thank you again for yourinsights.
Tucker Graves (08:07):
Absolutely Thanks for having me.
William Gladhart (08:11):
Thank you for joining us on the Leadership
Levers podcast.
Find all our Leadership Loversepisodes on the Culture Think
Tank website at www.
theculturethinktank.
com or listen on your favoritestreaming platform.
We'd love to hear from youabout the challenges you have
faced as a leader.
Tune in weekly as we inviteleaders to share their
(08:35):
experiences in strengtheningculture and performance, one
action at a time.
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