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[EO San Francisco] Building a MultiMillion-Dollar Immersive Theater Business With Nick A. Olivero

Nick A. Olivero

Nick A. OliveroNick A. (Ollie) Olivero is the Co-Founder and Executive Director of Boxcar Theatre, a production company specializing in immersive and interactive theater experiences. He is also the creator of The Speakeasy, a long-running 1920s-themed immersive show in San Francisco, and has produced over 60 live experiences, including magic shows and haunted houses. With over 25 years of experience in theater, Ollie has raised millions of dollars in funding, built large-scale productions, and expanded into venue management and corporate events.

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Here’s a glimpse of what you’ll learn:

  • [02:45] Nick A. Olivero’s journey from theater kid to immersive theater entrepreneur
  • [05:27] The transformative power of theater and creativity
  • [07:03] Why immersive theater gained traction and how Ollie adapted to the trend
  • [09:55] Finding the perfect venue and shaping The Speakeasy around it
  • [12:15] How Ollie raised $1.5 million and secured a loan to fund a large-scale production
  • [14:23] The unique elements of The Speakeasy
  • [18:59] Overcoming financial collapse and rebuilding after the pandemic shutdown
  • [24:59] Ollie’s mindset shift from high-risk productions to sustainable event models
  • [31:27] The growing demand for real-world, in-person experiences post-pandemic

In this episode…

Attendance is declining in traditional theater, and immersive experiences are emerging as the new frontier. What does it take to build a multimillion-dollar immersive theater business that keeps people coming back?

Visionary immersive theater creator Nick A. (Ollie) Olivero says that engagement comes from blending artistic innovation with business strategy. While immersive theater can be a powerful experience, it must also be commercially viable to survive. Ollie’s journey began with small experimental productions and evolved into large-scale, interactive experiences like The Speakeasy, which required a $2.5 million venue build-out and $1.5 million in fundraising. He maintains that understanding audience psychology, creating memorable real-world experiences, and adapting through challenges have been critical to sustaining and growing his business.

In this episode of the Rising Entrepreneurs Podcast, John Corcoran sits down with Nick A. (Ollie) Olivero, Co-Founder & Executive Director at Boxcar Theatre, to discuss how he built a thriving immersive theater business. He shares how he built The Speakeasy, the strategy behind turning theater into a sustainable business model, and how he successfully raised funding for large-scale productions.

Resources mentioned in this episode:

Quotable Moments

  • “I always knew that I wanted to start a theater company, and when I graduated college, that’s what I did.”
  • “I don’t think people knew that they wanted to put their phones away, but when they did for The Speakeasy, they would thank me.”
  • “It’s not just a show. It’s your night out… We’re part of your night out.”
  • “Magic is very approachable… I want to build more of those.”
  • “Creativity is just creativity. I get excited about expansion and bringing a theatrical spin to events.”

Action Steps

  1. Prioritize experiential learning: Participating in immersive experiences helps individuals step out of their comfort zone and fosters creativity.
  2. Embrace flexibility and adaptation: Nick A. Olivero’s journey highlights the importance of adapting business models to current trends and audience needs.
  3. Foster community connections: By creating events where attendees can disconnect from technology and engage directly with others, you nurture a sense of community and belonging.
  4. Focus on storytelling: Incorporating narratives into your products or services captivates audiences and enhances their experience.
  5. Evaluate and iterate: Regularly assessing your initiatives and making improvements based on audience feedback ensures your offerings remain relevant and appealing.

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Episode Transcript

Intro 00:03

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

John Corcoran 00:13

All right. Welcome everyone. John Corcoran here I am, the co-host of this show. And you know, today we’re going to be talking with the visionary behind the speakeasy immersive theater experience in San Francisco, Nick A. Olivero. And you know, if you listen every week, we have interesting and smart CEOs, founders and entrepreneurs from all kinds of companies. We’ve had Netflix, we’ve had Grubhub, Redfin, lots of great episodes that I’ve done before, and I love being able to talk to smart entrepreneurs. And of course, this episode brought to you by EO San Francisco, which is the Bay area Chapter for Entrepreneurs Organization, which is a global peer to peer network of about 18,000 influential business owners across 200 chapters, 61 countries, and the Bay area chapter has about 110 members in industries ranging from marketing to agriculture to tech professional services. And if you are the founder, co-founder, owner or controlling shareholder of a company generating over $1 million a year in revenue, and you want to connect with other like minded entrepreneurs. Check us out. You can go to eonetwork.org/SanFrancisco to learn more about us. And I am the co-founder. I’m a member of EO San Francisco and the co-founder of Rise25, where we help businesses to give to and connect with their dream relationships and partnerships. We do that by running your podcast. We are the easy button for a company to launch and run a podcast, and you can learn about what we do at rise25.com. All right. Let’s talk to our guests. So Nick Olivero. Ollie, as I know him, he’s a visionary creative director and producer known for his contributions to Vision Immersive theater. And he’s the creator of The Speakeasy, which is a highly acclaimed interactive theater experience that really transports audiences to this vibrant world of 1920s era speakeasy. And it’s a really cool experience. I’ve been to his venue before and I can highly recommend it. He’s also got another venue, which is the Haas-lilienthal House, where they run that venue. It’s a historic mansion and museum and then also use it for their own productions. They have other productions like they had a Halloween one and a Christmas one, and we’ll talk about that as well. Ollie, happy to have you here today. And let me start. I love to get to know my guests what they were like as a kid first. And I know you weren’t a budding entrepreneur who was going selling, you know, gum to your classmates in third grade or selling weed in high school and getting busted by the principal, like many of my past guests have. But you rather were a theater kid, which eventually, you know, ended up leading you to the world of entrepreneurship. But tell a little bit about what you were like as a kid. You were out there like putting on performances with your friends, rallying a bunch of friends.

Nick A. Olivero 02:45

Of a theater nerd. I kind of got into when I was in middle school, actually. Before that, I remember watching as like a 8 or 9 years old. My my siblings would I’m a little bit younger than them. there four, six and eight years older than me, and they were always putting on shows. We had a very active youth theater at church, and they put on puppet shows and plays and stuff, and I was never in them. I was always watching them, and I never really scratched that itch, so to speak. So I kind of caught the acting bug from watching my older siblings act. None of them are in theater now. They kind of got it out, but ended up in middle school and just started doing from variety shows and, you know, different skits and such in the shows and wasn’t necessarily cast as the lead. So, you know, I was a little fat kid. So but, you know, I was the funny, I was the funny fat kid.

John Corcoran 03:40

And I it was a role for a funny fat kid.

Nick A. Olivero 03:43

It was always a well, those work really well when you’re older, you know, not when you’re doing the ingenue role. They work better in your older years when you are doing sketch comedy, which I did get into after college and did five years of the sketch comedy group Killing My Lobster, and I was the fat funny guy in that. But in any event, you know, I would help with the sets and doing stuff like that back, the kind of production stuff, and then just kept doing it. Then all through high school would start directing productions, one act plays. We did a murder mystery and ended up going to college for it. So I didn’t really go into the my, you know, my dad was in sales. He he was a bit of an entrepreneur. He had a few different businesses. And helping him do that growing up was more of a chore than it was a, you know, something we did. So it’s always been around, you know, he wasn’t really good at being an he wasn’t a model employee. He was he was a bit too smart sometimes and a little too clever and was always getting fired for various reasons. And so I think I followed in his footsteps. I wasn’t a very good student in terms of listening to my teachers. I kind of did my own thing, which Was both good and bad. But yeah, I, I always knew that I wanted to start a theater company. And when I graduated college, that’s what I did. And within about a year and a half, I had a company started.

John Corcoran 05:10

And what drew, what drew and draws you to this day to the experience of theater? Is it the excitement? Is it the, you know, entertaining a crowd? Is it bringing people together and the connectedness that you have? You know what what drew you personally?

Nick A. Olivero 05:27

It’s you know, I’ve had so many weird, interesting conversations over the years with people who are, you know, legit a star, celebrities, you know, from Neil Patrick Harris to, you know, the drummer from No Doubt who have this weird kind of I don’t want to say envy because they have great lives, but just having my own company, being able to do my own shows, thinking that that’s some sort of freedom that you don’t necessarily get when you have a certain kind of publicist that has to maintain a persona. And even, you know, company people make more money than me who are like, wow, this is so cool what you do. You know, I have something to talk about because you can actually experience my product. And and I didn’t used to talk about it as a product. I’d say show my play or whatever. Now I take a little bit more product approach and but I think at the beginning it was really just about trying to, yeah, create experiences for people and affect change. I mean, really as, as idealistic 20 year olds you can get, you know, I want to change your mind, your heart, your soul. Yeah. Sometimes that’s your comedy. A lot of times that’s drama and thinking. My shows used to be much more esoteric and in nature or more dramatic, and they’ve over the years, also, as I’ve chilled out, have become a little bit more about just having a great night out, being able to forget about your troubles and forget about those, those kind of.

John Corcoran 06:52

So important, so important these days. What what drew you specifically then to the immersive theater, because we’re not just talking about normal theater. This is there’s a you have a different spin on things.

Nick A. Olivero 07:03

Yeah, I started doing this. It’s a it’s a bit of a buzzword now, but it wasn’t when I started doing this. I’ve been doing it for 25 years or so, and it was a very emerging field. So I was a little unlucky that I because I’ve been from the beginning and it was happening in, in London and New York, I was the only one doing it, but it was kind of a collective. I always say it’s like the building of the pyramids, you know, why are there pyramids and all these different? It’s like in the ether. So, like, immersive theater is very much in the ether. And I was doing it in San Francisco very much by myself and able to kind of earn a niche in there. That other people now it’s they’re kind of breaking in. But I have a big track record for it. You know, I was I used to be a writer, theater and work on new plays, and no one would come and see him. And San Francisco is known for its new plays. Sam Shepard wrote all of his work here in the 70s. And I want to become a director’s theater and reimagine classics. And and I started that show shut down because I was violating copyright infringement, stuff like that. So then I kind of moved into, you know, this I always had kind of interactivity and site specific in some of my work. A lot of it was out of necessity because we didn’t have a place to perform. So you create a place to perform and that just slowly, over time, evolved. I had a very influential conversation with Tony Piccione, who’s the artistic director of Berkeley Repertory Theater. He did Angels in America, which is a very, very famous two part play, that movie, and basically discovered that, among other great productions, launched American Idiot, which was, you know, went on Broadway, Green Day’s American Idiot show. And he basically said to me, he was like, there’s no way you’re going to build a regional theater the way I did in the 80s. You’re going to have to figure something else out. And that was 2008, and it really clicked with me that I had to to be in order to build a company. I was just struggling and struggling as most artists do. And, you know, doing shows for free. And one person would show up as I hit my 30s, was approaching my 30s. I knew that this was not sustainable. And most people quit doing theater around that time because it’s not sustainable. And I started moving towards how do I keep this going? And I found this thing and I started looking for shows that would be more commercial in nature as opposed to just artistic, and started trying to find the sweet spot between my art. I tell my team, now, let’s not worry about the art like I can do the art part with my eyes closed. I need to find somebody that’s going to sell tickets, stay and keep the lights on basically because it’s all.

John Corcoran 09:45

And so how did you settle on this idea of The Speakeasy? And I know that it was part of it was you found this venue which came first, the idea or the venue?

Nick A. Olivero 09:55

The venue.

John Corcoran 09:56

So you had the idea.

Nick A. Olivero 09:59

I had the idea in 2006. And then I did a, I did a production of Little Shop of Horrors, which became a little infamous because it got shut down for all of the changes I made. And the president of the, of the rights company came out and saw it. And it was it became a national article about copyleftist. And I’m a copy leftist. I just don’t believe in that kind of, you know, I don’t think Mickey Mouse needs to hold a copyright for a thousand years. You know, he’s not. So I have a very radical view on that. I still do, and I let people use my work anytime they want because it’s not what the words. It’s the word. 

John Corcoran 10:36

Experience. Right. 

Nick A. Olivero 10:39

Yeah. You still got to create the thing. Yeah. And I so I had this idea for this show. It just kind of came out of nowhere. A lot of times my ideas for shows come out of just me sitting on the beach. Yeah, in the shower, it doesn’t matter. But I decided to do this because I was like, I like, I need to do something that the copyright there’s no copyright for. And I was like, oh, when? When was copyright invented? It was 1923. So that’s when I set my show.

John Corcoran 11:06

Yeah.

Nick A. Olivero 11:06

So it’s funny and it’s really it became ten years of my life was doing the show. So it was a bit of a it was kind of.

John Corcoran 11:15

Can you mention that you wanted something that would sell tickets? Did you have a hunch that people would be interested in this kind of idea?

Nick A. Olivero 11:23

It seemed right. But, you know, I think everything I do is going to sell. I’m proven wrong most of the time. Yeah, but we really went all in and I had a space. We converted it. We did.

John Corcoran 11:34

Yeah. Talk. Talk about this space too. Like, would this space that you found, what it was before and how you converted it?

Nick A. Olivero 11:40

So the proof of concept was in the tenderloin, and it was a it used to be office space and studio space. We did the show there for five months, sold it out, and then we went on the hunt for a permanent venue because we knew we had something and we were a A little naive to to think that it was just going to be, you know, who knows. So we went and found this venue in North Beach. It was a single screen movie theater.

John Corcoran 12:07

And it’s like subterranean or something. Isn’t it?

Nick A. Olivero 12:09

It was just a It was an old single screen movie theater about. 13 years, but it had been 13 years.

John Corcoran 12:13

13 years. Wow.

Nick A. Olivero 12:15

Yeah. It, it the columns were far enough apart where I could. I needed space. And it was hard to find space in San Francisco that’s prone for earthquakes. There’s columns every 16ft. So it ticked off a lot of the boxes. Not all of them. And the developers were just key to making it happen. They they got it. We got a loan from the bank, which is unheard of. Yeah, we had no collateral or anything. And we did a $2.5 million build out for this venue and another million dollar raise for the show. So it was a huge production and huge.

John Corcoran 12:45

So you raised a million bucks.

Nick A. Olivero 12:49

We raised a million and a half and took out a loan. Yeah. For a million.

John Corcoran 12:54

And what was that like? Was that from family and friends? Were you just scraping to get a dollar from whoever you could?

Nick A. Olivero 13:00

It was a lot of audience. It was people who had either seen previous shows or just liked the idea. We we launched it like we would.

John Corcoran 13:09

Kind of like a Kickstarter?

Nick A. Olivero 13:09

From the 

50s. I would get up there and on stage, I’d invite them to the to the raw space on stage and just pitch and talk about what I was going to build. And I, you know, had the the fever of a madman. You know, my eyes were burning red with passion. And he bought it hook, line and sinker, you know.

John Corcoran 13:3o

Yeah. Yeah. That’s so cool. And so and so you spent you spent 2.5 million building out this space. So describe it to everyone. Like how you transform this space and what it looks like now.

Nick A. Olivero 13:42

Well it used to have like a, you know, like a movie theater, a gentle slope that went down. So we, we had to level it out. So we created two levels. Put a little small stair step. It’s not a lot staircase but few steps and a ramp down one side for Ada and we level it out with concrete, rebar, foam, all of that. And we built a cabaret space, which is pretty big. A casino, which was part of the show was gambling, even though it’s for entertainment purposes and a couple of different bars, and it’s about it’s a little less than 10,000ft² and the audience could go wherever they want. It was a choose your own adventure. We ended up running the show for three years, which.

John Corcoran 14:20

I have to mention there’s a secret entrance, but I don’t want to give it away to people.

Nick A. Olivero 14:23

Secret entrances. Yeah, yeah. One 2:00, another one through a laundromat. We would bring audiences down to the alley I had we used to have this rat in the cage that when you go down to the alley like the rat was caught and we had a live rat. It was just so bizarre, all this weird stuff. And I just wanted to do. We took everyone’s cell phones away so you couldn’t use your phone, and we didn’t use computers, so everything was done with pen and paper. It was very complex.

John Corcoran 14:50

Yeah. So you you eventually simplified these.

Nick A. Olivero 14:53

We did because it wasn’t. They had 35 actors in it. We ended up cutting it down to 20, 25 just because so many mouths to feed. And it’s still an expensive show to run. So we ran it for three years. We’ve closed it, we brought it back, we closed it. What we ended up with is this beautiful venue that we now use for events and weddings and holiday parties, corporate corporate events, kick off sales kick offs, which is a much more sustainable business model, sustainable business model that I always tell people when we do an event, we know how many people are going to come, so I know how much money I’m going to make and I know who the low profit margins are built in. What we do is I do the same show on a Wednesday night and I do on a Saturday night, except they usually have to reduce my tickets on a Wednesday night and it’s not a sellout. So the profit margin is a sharp decline, but my expense is the same to run that show. That’s why the theater model isn’t the best model. Unless you’re Hamilton where you can project what you’re selling six months in the future. So there’s a lot of gambling involved in this, and it’s short term. It’s like going to the pass line every roll. You know, when you do theater, you just don’t know.

John Corcoran 16:07

You know I we had an, you know, alchemy conference. The creator of Meow Wolf, one of the creators. The CEO. Yeah. He came and spoke and he talked about, he said something weird about Americans is just if you give them a like, you can climb, they want to climb through a fridge into another world. And they’re just like, lose their minds over that. You know.

Nick A. Olivero 16:29

I used to go to school in Santa Fe. That was my old bowling alley. And it’s a bunch of burners they have. They had no idea what they were doing when they did and didn’t know what I was doing when I did it and why that became. The. Thing is, a bajillionaire. I mean, they, they, they got wolves everywhere. Why that’s in there and there. And not to the speakeasy? No idea. Yeah, it was at the right place at the right time. And that’s the problem with art is you can’t. There’s no algorithm formula. Right. And there are companies out there who are trying to do it that you will not be able to. I will never be able to anticipate what we feel.

John Corcoran 17:11

Well, that’s an interesting thing because there’s so many companies that are afraid of AI now and how it will be a threat to their business. But for your business, which revolves around an experience and you get drinks and you’re around other people, whether it’s a corporate event or a theater event, and there’s, you know, performers that are there, you know, I don’t really see AI being a threat to your business, do you?

Nick A. Olivero 17:34

Are you kidding? It’s a it’s a tool, I love it. I write scripts for me now. I love.

John Corcoran 17:38

But I meant I meant like like replacing your business or. Yeah, or like a threat to your business.

Nick A. Olivero 17:45

Who was it? What’s his name? The guy who wrote Taxi Driver. What’s that guy’s name? He was just on there saying that AI is a better filmmaker than some of these artists, and it got a lot of flack. I don’t agree with that. It’s hard. I don’t know, they can come up with ideas, but it’s it’s.

John Corcoran 18:04

But you still got to hire the actors. The performers. It’s the experience of it.

Nick A. Olivero 18:08

Right? You can’t outsource that. I mean, especially in mine. We had a physical space, too. It’s good that people are like, oh, you can expand. Its expansion for me is brick and mortar. It’s it’s a challenge to expand. And there’s always an upfront cost to expand to another venue. You know, we hope to have three venues in San Francisco and then maybe move, you know, have venues in Austin, Chicago and so on and so forth. But it’s that requires boots on the ground. It’s very different than than a digital, you know, a podcast or whatever it may be. You know, there’s a digital footprint. So now it will always be the case.

John Corcoran 18:45

You and I had a conversation about your Covid experience. You know, like like so many businesses, but especially yours You, you know, were shut down by Covid. Take me back to March of 2020. And what that was like for you when that happened?

Nick A. Olivero 18:59

Yeah. Post-traumatic stress. Yeah.

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