Utter the name “Malnati” and every Chicagoan in earshot will immediately sit up a little taller. 

And Will Malnati is, indeed, from that Malnati family. His great-grandfather Adolpho ‘Rudy’ Malnati, Sr. was a deep dish pioneer at Pizzeria Uno, and his grandfather Lou opened his eponymous restaurant in 1971 — the first in a chain now widely considered to serve the best deep dish pizza in Chicago (and therefore everywhere.) 

Will is understandably proud of his heritage, and of the lessons he learned watching his father take over and run a wildly successful restaurant business. But after spending a decade in the family industry, Will’s path ultimately lead him to the less glamorous but equally challenging world of podcasting. 

In 2019, Will started At Will Media, creating podcasts and other audio products for companies who want to get in on the latest ways to connect with customers, with the help and guidance of an expert. I caught up with Will over the phone, to talk about transferable skills, learning to delegate, and planning for the future.

A brand new venture

Scott: I think your experience and your life will tell the story of why you’ve been successful; but tell us a little bit about At Will Media.

Will: I started four years ago with the idea of producing podcasts. It was still pretty early in the podcast industry. I started going up to celebrity friends of mine or people with great personalities that had big blogs or something. I was trying it out and funding it myself. And then I started selling ads. 

After about a year and a half of that, I was looking at this business model like, ‘Huh, this is a tough business.’ It’s tough because it’s too long of a runway. Unless you are the 0.001 percent of shows that are garnering $500,000 per episode, it’s a difficult situation to be in. 

At that same time, I was asked by Entertainment Weekly, ‘We want to be in this podcast space, we’re not really sure how to navigate it, can you help us?’ And at that point, I said, ‘That’s not really something we do, but okay, sure, we’ll help you guys out.’ And as we’re doing that, I was starting to learn that brands — specifically publishers — need help. They want to be in this industry, but they’re not really sure how to do it right, or how to do it uniquely, or how to build a product that matters. 

I started asking around, to a lot of the people I’d met in the restaurant industry. If you’ve ever been in the restaurant industry, you shake hands with every walk of life in every industry imaginable. And so I had a starting block to reach out to different brands. I started doing that, and all of a sudden, brands were like, ‘Oh yeah, we want to do a podcast. You guys will help us? That’s great.’ And they started cutting checks to me! 

I was like, hold on a second: what am I doing trying to grab this ad for whatever dollars? I’m going to really lean into this branded content, because there was clearly a need for it in the market. I was able to start building a team with the money from these different brands, and soon we had some big brands coming to us.

People will say, ‘How did you get from the restaurant industry to the media?’ I’ve always been interested in media. I understood the tech side. And at the end of the day, hospitality runs through both of these industries. I learned how to really be hospitable through my years in the restaurants, and now we are this 12-person podcast production shop based in New York that focuses on being hospitable with all of our partners, and really being an extension of these big brands that want to be in the podcast space. 

The Malnati school of business

Scott: I’m going to guess that as a kid growing up, you’re watching this Lou Malnati’s empire and thinking, ‘Here are things that we could also do,’ whether it’s a fit for that brand or something down the road. Obviously it was down the road, as you’ve had several successful brands. Talk to me a bit about what it was like growing up in that kind of environment.

Will: When you’re a kid, you’re so immersed in it that you don’t really realize it. I was in the kitchens running around as a toddler, and I started working the phones at 11 or 12, and at that point the business was really growing a lot so I was able to watch that happen. Every two, two and a half years, a new location would open. Watching my dad grow and learn from mistakes, I was essentially learning alongside of him. 

My dad was coming out of college right when his father passed away, and it wasn’t like he had the luxury of deciding whether he wanted to go into the business or not. Someone’s got to go in the next day and run this thing. So he found himself in an interesting situation where he hit the ground running and started figuring out the business. It was definitely an uphill battle for a while. 

He came out on the other side deciding to grow this business in a smart way, focusing on the product, and the quality, and the people. Other pizza businesses franchise out; that wasn’t his style. He wanted to really make sure he had his hand on the wheel at all times. And so I was able to watch that, and I’ve definitely adopted a lot of that in my own entrepreneurial career. I don’t want to be the guy that rushes into this explosive growth, who is trying to bite off more than I can chew. I want to be smart about growth. I want to be smart about capital, I want to be smart about the people I hire. And so those things were instilled in me super early on.

Scott: How do you decide when and how to bring in people to take things off your plate?

Will: It’s a good question. I actually needed someone to tell me, ‘Hey, you are now in this stage of your business when you need someone to be an extension of you.’ It’s like, this is my ops person who can run these things, so that I can be looking forward. 

I think one thing that I’ve struggled with in the past, and I’ve gotten better at over time, is really understanding when and how to step back from everything and visualize where I want to be. That’s something my dad is amazing at. He can look ahead 10, 15, 20 years. And that’s something that I haven’t been able to do that well. So to be able to step back and look at it like, ‘Okay, rather than what do I want the next hour to look like, or what do I want this week to look like?’ looking back and saying, ‘I’m going to pause all this madness. I’m gonna let someone else run the ship for a little bit while I think about where I want to be in five years.’ That’s been a huge learning curve for me. 

Facing the future

Scott: If you could highlight one thing that you think was the best lesson that you’ve had yet, what would that be?

Will: The capital raise always comes up. For the past four years I’ve done everything I can to not have to raise outside capital. To your question, I really learned what it takes to bootstrap. I didn’t want to have investors. And now, with an industry that’s growing, and that VCs are becoming involved in, and have an appetite for investing in, do I now take that next step and raise capital for hypergrowth? I don’t know. And so I’m in the middle of learning what the best next move should be. The choice for me is going to be, do we move forward and keep using our own cash flow to build this thing, or do we try to go at it like some of these other companies? 

I’ll always have a voice in the back of my head, questioning whether I should be going down that road, or whether I should stay true to how I envisioned this from the beginning. We’ve done great, we’re going to continue to do great. We have a massive second half of the year coming up, as well as the first quarter next year. So we’re going to keep growing and we’re going to keep doing this thing.