330 - Suitcase CEO: How a Love for Travel Became a Thriving Brand with Anemoia Media's Henry Woodman

Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Henry Woodman, welcome to Listening with Leaders. I looked at your LinkedIn profile and you're kind of like me. You've done everything. So, let's start off. What's your backstory, man?

You just said it. I've done everything.

It's funny.

No, I don't really know that I've done everything. I've just pretty much been, I guess you could say, a hedonistic or opportunistic entrepreneur. So, I do things, at least I did things in my misspent youth that I loved or I wanted to do. And really, hey, there's an opportunity. I think I could make something of that or do something with that. That was the, the focus. I was born in South Florida and then I moved to, I went to college in Arizona, but I won't ramble on. If you have questions, go ahead and tell you.

Well, you, you've been in the media business in many different ways. And what I, what caught my eye was, and I, you need to help me understand this. You were doing film, like either sales films or documentaries or something for a whole bunch of companies that were in the travel business or in the hospitality business. Tell me. Yeah. And that sounds like you got to go to some pretty cool places and film some pretty cool stuff. Oh yeah.

It's like my, my dream, at least when I, first of all, when I was younger, I studied and I didn't study. I thought I wanted to be an architect. And at 15, I got an internship and I saw that they had to use math. This is 1975, right? So I had to use math for the electrical and the plumbing. And I'm like, oh, that's horrible. I just wanted to draw pretty pictures.

Right.

So then at 16, I went to Honduras looking for a lost city. I then had ABC Sportsman film our adventure, and I thought, this is so cool. This guy's— the director at the time, he was 24, I was 16. I said, he's traveling around, he's having fun, he's not sitting in a desk job. This is what I want to do, right? So I go to college in Tucson, I study radio and television thinking one day I'm going to move to Los Angeles, I'm going to get in the film business and be a big-time film director, producer. That did not happen. But while I was there, I had made a little bit of money in college in a small business I started. Then I went to LA and I got on a game show and I won some money there. So I'm like, okay, I don't really need that desperate to work and I don't have a lot of bills. Eventually that money ran out and I thought, okay, I gotta do something. I started working as what's called a PA, a production assistant on a film crew that would travel doing travel logs and travel documentaries. This ended up being somewhat of my focus for almost 10 years, where I went from PA to sound assistant to the sound guy, and eventually I'm producing travel films. And in the early '90s, soon after Pinochet in Chile had left and it went from a dictatorship to a democracy, they ended up becoming a more democratic country with TV stations that were added, a new network. So we had done some films for Eastern Airlines in Chile, so we knew the production company. I called them up, I said, listen, I'm gonna come down there and I'm going to pitch a game show to this new television network. Sure enough, I'm down in Chile, I pitch the game show and they pick it up. So 2 months later we're in production, we're starting to put together, and I'm thinking, okay, let's sit here for a little while. I'm in Chile, I'm producing this game show that— an idea that I ripped off from a US show. And somebody hands me a CD-ROM and I put it in the computer. This is the mid-'90s now. And I look left and right and all around and up and down and I'm like, oh my God, that is It's a virtual reality tour. And that was, for a guy producing travel films, that was just too cool. And I'm thinking, wait, I can do a company without having to travel with all these guys and 17 pieces of luggage? I'm gonna produce virtual tours. So I set up a company called World Travel Vision, and we were one of the first to do 360 tours of destinations and hotels. Oh, wow. So eventually the hotels say, how do we get this? Now we're in the late '90s, right? Or mid to late '90s. That how do we get this stuff on this new World Wide Web thingy? I don't know, send them a CD-ROM. Because I would send them, or I would give them CD-ROMs that they would give away at trade shows and conferences to promote their hotel or destination. So eventually I'm like, all right, let me see what I can do to help. Now I had no idea about the distribution of content in the travel industry, the rate and the availability. You'd show up at a brick and mortar agency, would tell you here's how much that hotel is for sale on that night. No pictures. Now the internet comes along, even though it's slow at the beginning, but they're starting to say, we need photos, show me what this place looks like. And so there was no capacity with those systems, those reservation systems, to deliver photos. And so eventually I went from virtual tour production to virtual tour production and distribution to virtual tour production, distribution, and photo production, distribution, and then eventually We ended up— now if you go to any travel internet site on the planet and photos of pretty much any hotel, they would have come from my servers or my— the company I—

wow.

So that was the evolution from wanting to get into the production business to running a tech company. And I don't— I couldn't write a line of code if you put a gun to my head, so I just figured there was an opportunity and I could make some money.

Wow. So what are you doing today?

40 years ago when I wanted to produce a movie, I ended up buying the rights to a book and I didn't produce a movie, but I kept that book and I just published it last summer. It's already doing really well. It's won some awards and now I'm developing the concept of the book into a series for streaming. It's called Slip It.

Wow. Yeah. Okay. So grass doesn't grow under your feet. What is it that gets you up in the morning and gets you excited to do all this stuff?

My dog having to go out and pee. No, yeah, you know what, I've always been a— no, that's not true. I've usually been a morning person. Maybe back in college when I'd spend a lot of debaucherous nights, I didn't get up that early. But I was— I think the thing that I've always done is getting up early I used to be a swimmer. We would have morning workouts and evening workouts, and you kind of get that discipline. And so now, you know, I'm up early just because I need to go work out or do something, and then I need to focus. Listen, at this stage in developing a series, it's really a lot of knocking on doors and asking other people, hey, I want to be the executive producer. I don't really know enough to be a producer here. I own the IP. Let's go forward with this. And so that's the stage we're in right now in development. Wow.

Amazing. What gets you excited? Just doing new creative stuff every day?

Yeah, it's funny. I like learning things. What gets me excited really is new things. It's like the ADD mindset where you're like, okay, I've learned a little bit about that. Next. And I think that's the thing that, at least in today's age when there's so much information on the web, on podcasts, on books, that I just, I like listening to podcasts. I like listening to books. I like learning. And even with the TV production, the world is changing very rapidly with AI in every vertical, including the production of film and video.

Oh, it's crazy. Yeah. So what do you think it is that's about you that has made you so successful in all these different ventures?

I'm gonna be really honest. For the most part, luck. I mean, there's a lot of discipline.

I appreciate the honesty. Yeah.

Listen, uh, white guy born in the US in in the '60s. How bad could I screw that up? With a little bit of discipline and tenacity, but as importantly, I think people will say, oh, you were at the right place at the right time. I'm like, yeah, most of my life I was at the wrong place at the right time, or I was at the right place at the wrong time, and I just happened to meander around. When people say I'm looking for the right thing, no, the right thing, if you continue to go out and look and things come to you, if you would've said decades ago, you're gonna be running a tech company, a global tech company. I'm like, please, that's the last thing I'm gonna be doing. So I think that first finding the opportunities that you're solving a problem, right? Because that's an important one. And I always tell people, listen, if you are lucky and prepared, you might see opportunity drive by that corner. If you're standing on the corner and you're not prepared and you're lucky, you may not see opportunity. And vice versa. If you're prepared, but you're unlucky, again, luck plays, you know, when people say, oh, I'm really smart. Yeah, I know.

Luck is a huge— that's right. Hold the thought. I gotta step out just for a second. I'll be right back. Henry, I wanna pivot to the topic of the show, which is listening with leaders. And if you, I think you did a little bit of background research on me. I'm a lawyer turned peacemaker, and I teach people how to listen. And I'm just curious how you learned how to listen.

I don't know that I learned as much as I was forced to, because early on in starting the business, you have some preconceived ideas. You hear stories like my father would say in his business world, ah, meetings are a waste of time. And I didn't have meetings, right? Because it was a waste of time according to my father. Eventually, as I start to say, okay, what actually do I need to learn in order to put the tools into this business, get the processes and the procedures right. I literally went back to school in my 50s and got an MBA in entrepreneurship.

Yeah.

And I was handed a book as well by Gino Wickman called Traction. So those things basically, I guess, simplified— this gets to the listening part in a second— simplified the Here's what you need to do. And so what I then did is I said to each one of the employees at the time, we were relatively small, I said, here's the book, read this. We're gonna back together in a month and this is our Bible, right? And all of you can provide feedback and input on how we're going to move this forward. What's our vision? What's our mission? What would people would say early on, you gotta have the right people. And I'm like, I can't even afford to pay myself. You want me to, the right people? I didn't understand that meant culture and what is the culture, right? And then you have to have a KPI or KPIs. And I'm like, okay, I didn't know what a KPI was, and I have to learn. And then that means you have to listen. Okay, you just like a good producer, more about your job than I do. So I'm going to listen, and then we're going to work together to try to make that move forward, right? I think it's— there are very few people who know everything about every component of the business that can't that can move it forward. You've gotta listen to the people that know more about you and trust what they're saying as part of the team.

What motivated you to go back to school in your 50s? And the reason I asked that is because I went back in my mid-50s to get my master's degree. And I'm curious what your story is.

Yeah, the motivation was first, I was invited to do a presentation to a group of CEOs when I started the business and around the room, there were a bunch of MBA students, and there I stood in front of all these guys and the students thinking imposter. The imposter syndrome was totally kicking in.

Okay.

And I thought, these kids around the room know more about business than I do, and here I am talking about a business thing. What a fraud. So I motivated myself to go back to school because I really realized I know what I don't know, and I need to know more in order to make that work because if I didn't, I probably would not create the foundational structure in order to scale the business.

There you go. Interesting. Yeah. I went back to school when I was 48 and it was in the middle of, it was the peak of my legal career trying cases and I decided to become a peacemaker. So I went back to school and earned my master's degree in peacemaking and conflict studies for exactly the same reason that you talked about.

And don't you agree when you go back at an age that you're really interested, you actually learn stuff. 'Cause I don't remember anything I learned when I went to college in my 20s, right? But when I'm in college there, I'm surrounded by much younger people who just want a degree to get out and get a bigger paycheck.

Check the box, right?

Yeah. And I'm thinking, you know what? I can apply this.

Yeah.

Oh, with this lean management stuff, I totally get this kaizen. And oh yeah, I got this, right? And it was really relevant because it was something I could really apply right then and there.

Amazing. That, yeah, that same thing. I think going back to school mid-career is something everybody should consider. Yeah.

And the other thing is the world changes. I would imagine going to school now and then coming a couple decades later, imagine what changes have happened, especially with AI. Oh my God.

Crazy. Yeah.

Yeah.

So where do you see yourself in 10 years?

Hopefully accepting my Emmy for the series that we're— yeah. Yeah.

No, I'm glad that you don't have any ambition. Yeah.

Yeah. I got Emmy nominations, but that was for local news stuff I did back in my 20s. And I figure get a real national Emmy for the series Slippin' that we're developing for streaming. That's 10 years.

Good for you. One more question, Henry, and I'll let you go. What's one thing about yourself that you haven't revealed to us yet that we would never know about unless you told us?

Oh yeah, you probably already guessed I was somewhat of a delinquent, but what kind of started this, and I look back, when I was 13, I went to a swim meet, I was a swimmer, in Mexico. I came back with a switchblade, right? Now you can imagine this is 1973. You could walk up to the gate, you could go on a plane with a knife. Nobody cared, right? So I come back to junior high and I'm pushing this button and the knife pops out and everybody thinks it's the coolest thing ever. So I get on a plane as a 13-year-old by myself, go to Mexico City, buy a couple of boxes of switchblades, come back and sell them in junior high and make a little bit of money.

So there you are, the entrepreneurial spirit at a very young age.

Exactly.

Which blades at that, which are illegal as hell now. It's—

yeah, the world has changed, but this is 1973.

There you go. It's been great chatting with you, Henry. Thank you so much. Wonderful conversation.

You got it. Thanks, Doug.

You bet. Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.