Leadership Levers

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

• William Gladhart

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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.

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William Gladhart:

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 Graves:

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:

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:

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?

Tucker Graves:

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:

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:

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

Tucker Graves:

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:

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:

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?

Tucker Graves:

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:

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:

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:

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:

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:

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

Tucker Graves:

Absolutely Thanks for having me.

William Gladhart:

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.

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