From Food Service to SaaS - Tucker Graves on Culture, Growth & Asking for Help

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.

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. 

Transcript

Welcome and Guest Introduction

William Gladhart 0:00

Welcome to the Leadership Levers Podcast . I'm your host , Will Gladheart , CMO at the Culture Think Tank . At the Culture Think Tank , we empower leaders with metrics that strengthen culture , drive performance and return . We're here today to learn about the actions leaders have taken to address organizational change . Today , our guest is Tucker Graves , CEO and co-founder of Pineapple Academy . Thanks for taking the time to join us . Thanks for having me . We'll begin by having you share with our audience a bit about yourself , your background and your organization .

Tucker's Entrepreneurial Background

Tucker Graves 0:39

Sure , my name is Tucker Graves . I'm the CEO of Pineapple Academy . This is my fifth startup . I guess I've earned the description of a serial entrepreneur . I guess there's other worse things to be called in the world of cereal , right , but I'm a third generation entrepreneur .

Tucker Graves 0:54

As far as I know , my grandfather started a protein distribution or manufacturing distribution company in Northwest Missouri , predominantly focused more on kind of center of the plate , meat items and things like that . Essentially , what he did well is he outsourced the butcher from the grocery store . My dad took the idea from my grandfather and said hey , hey , dad , why don't we sell the people who are already delivering these products to more stuff ? And he started down the road with things like frozen French fries and things that would work in the trucks that he had that supported those products . And my dad ended up becoming a pretty large family-owned food distribution company that he sold a couple of years ago . And then , of course , I think I was born into this food industry , so most of my companies have had some parallel , although this one , pineapple Academy , which is focused on frontline training and really in the hospitality and healthcare world , has started in food but has evolved now beyond that too . Hopefully that sheds a little light on the background .

William Gladhart 1:46

Yeah , absolutely . We'll be discussing three questions today as a warmup to our conversation . Can you share why you believe a healthy culture is critical

Why Healthy Culture Matters

William Gladhart 1:54

?

Tucker Graves 1:54

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 the company , and it speaks to one of the metrics we should all look at and measure , because it's the baseline and the foundation . A company really doesn't exist without the people , and so company is just a shell where people all work . In my mind , if the culture is healthy , the company is healthy . There was a great consultant that I had he's one of our advisors , and we were in the process of raising money and he said it's really a simple formula . He said if you want to raise money , well then you have to have growth .

Tucker Graves 2:27

And they call traction in our world right . And he said and that's actually a very simple next step , because in order to have traction , you have to have the right people . And he said so the formula is simple Investments come from growth , which come from people , and so if you kind of think about it , you just keep going down . And so I remember my dad asking me one day . He said if you could pick one person to hire that you think would impact your company the most , who would it be ? And I said somebody in the world that helped create the best environment for people , because I believe that that would then end up resulting in the best performing company , if I was the best place to work .

William Gladhart 3:01

Yeah , I think that's really wise advice , especially from someone who's been in your industry a lot of years but also has started multiple companies . We hear over and over from leaders right people , right seats , right roles and also the clarity around the role and how they're impacting the organization is absolutely critical . It's been our experience that leaders tend to struggle in three key areas people , process or profits . In your role as a leader , could you identify which one of these three areas represented a cultural

Pivoting to Software: Process Challenges

William Gladhart 3:31

challenge in your organization or one of the organizations that you started ?

Tucker Graves 3:36

Sure , I think it's interesting because of those three . I think , as you just said , it can kind of change throughout your career path . I think we can probably say we probably struggle at different points with different things . I would say my current one with Pineapple Academy initially was process . My co-founder , greg , and I , like I just mentioned , we're food guys and so food guys know food things . And so we started out as a company that created content for the food industry and we knew the information but we didn't know how to package it or fancy words like the instructional design . And luckily Greg had been a teacher he was a chef instructor at a university , so that gave us a little bit of background .

Tucker Graves 4:14

But I would say that the process of how to run which we became a software company because we had put our content on a learning management system and a big health system came along and said hey , love the content , can't use your software . Is there a way to somehow get your content in our system ? And so we called an old friend who had helped me with previous companies . We had to figure out a way to stream it and protect our intellectual property and support the subscription model . When all that came about and we ended up pulling it off . Greg and I were kind of looking around , we're laughing and we're like holy cow . We're a software company and when it came to the operations of a software company , we didn't know what we were doing .

William Gladhart 4:50

I would say process for sure . Yeah , well , obviously the process element trickled into people and profits and growth , because they're usually all connected . I think it's interesting that you not only made the pivot from that full instructional to training and to software . That's a big shift . Was there any specific challenge that negatively impacted the organization , either through growth or that process piece ?

Leadership Through Vulnerability

Tucker Graves 5:16

Oh for sure , you know , as I mentioned , the very fact that we didn't know what we were doing , I think that was the biggest impact to the company , the culture of the company , the people we were hiring .

Tucker Graves 5:25

We just knew what we knew and we've run into that in our jobs in the past where , you know , greg kind of jokingly refers sometimes to folks in the food service industry , especially when it's not their core business , like a hospital , right , they're in the care business and how does somebody know how to manage the food service operations when it's not the core business ? And so it's this idea of the blind leading the blind leading the blind , and I think the way to turn that around first is to admit it , because how many people have we worked for in our lives that kind of fake it till they make it when they should just be honest ? I think the key here is just the first step to this whole thing is just be honest , and so us not knowing impact our growth , that impacted our culture . We weren't hiring necessarily probably the right people , but I think the first step towards writing it was just admitting it and being honest about it .

William Gladhart 6:12

Yeah , I really appreciate that answer . Yeah , I think it's a . It's a challenge and struggle for leaders to . We hear all the time in the high growth industry fake it till you make it . I'm like , well , yeah , that's fine , but what happens when you actually have to put up or shut up ? And that becomes a whole different story and I appreciate that honesty . But I think that honesty about where the company is at really bleeds over into the culture and the performance of the organization as well . Is there one thing that you've identified or that you would share with other leaders that has kind of helped you on your leadership journey ?

Tucker Graves 6:50

Sure , I think the most important word is vulnerability . I think going back to admitting we didn't know what we were doing , the ability to be honest about it . But I think the idea of flipping the narrative that being vulnerable and asking for help is not a weakness , it's a sign of strength , and that I think that's probably the most important thing for any leader is number one . I'm always continuing to learn my entire life . I'm a lifelong learner . All my friends are , my partner is . I've learned more in the last five years than I've ever learned in my life , probably .

Tucker Graves 7:18

And the first step , after just being honest that we didn't know what we were doing , is being honest about the fact that we needed help . And so every time we hit a wall whether it's in business operations or people or profitability or anything , it's around this vulnerability and instilling 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's how Greg and I have gotten out of every situation is just saying hey , we just need help and not being afraid to ask for it . So I think it's the most important underlying thing . Obviously , there's things like empathy and all those things that matter , but when we're talking about how to right the situation for us with process , it was about being vulnerable to getting help .

William Gladhart 8:01

I like that , Tucker . I've enjoyed having you on our Leadership Lovers podcast . Thank you again for your insights .

Tucker Graves 8:07

Absolutely Thanks for having me .

Episode Closing and Call-to-Action

William Gladhart 8:11

Thank you for joining us on the Leadership Levers podcast . Find all our Leadership Lovers episodes on the Culture Think Tank website at www . theculturethinktank . com or listen on your favorite streaming platform . We'd love to hear from you about the challenges you have faced as a leader . Tune in weekly as we invite leaders to share their experiences in strengthening culture and performance , one action at a time .