Tony Lillios: 10:04
Scared. Or friends. It was like, these are people who are like, oh, this means business. And we kind of, like, calmly listened to what they were saying and asked them to politely leave after the conversation. But soon after, our clients came like the Cisco Dells and Apple’s came to our backing and essentially said, Ido, back off.
Like, we’ve invested in these guys and we want to continue to work with them. We’ll still work with you, but do not keep us from trading and building on the invested and all the, you know, the historical knowledge we’ve built up with these individuals over the past. And so they really kind of were whatever the metaphorical £100 gorilla in the room. Yeah. And stood behind us and were like, yeah, what they said.
But it’s like the classic. There’s so much insecurity when you’re starting a business like, you know, am I doing anything? Every dollar I make, I’m spending to buy another chair, another computer paying rent. Like, yeah. Is this even going to ever make sense?
Yeah. That episode was a little bit of like, wow, they bothered like, we’ve got their panties in a bun. Like, that was like like, I guess we’re up to something, you know? And yeah, that’s a.
John Corcoran: 11:20
Positive way of looking at it. You know, I mean, so many people, I mean, I started by being a lawyer practicing law for a firm, and then I went out on my own, and I was practicing law. And some of those clients came and sought me out, just like you. And that’s kind of the classic way a lot of people start in entrepreneurship is they spin off and start something related to what they did before. So for me, if the managing partner of my previous firm walked in the door and said, you can’t take these clients.
It would have been really disturbing. So that must have been a seminal moment for you.
Tony Lillios: 11:49
And we weren’t lawyers, so we really didn’t understand, like empty threat, real threat, empty threat, real threat. Like, are we really in trouble or is this just like, getting slapped on the wrist, like we, you know, we were under-resourced, under-resourced legally at that point, so we didn’t really know what we were doing.
John Corcoran: 12:06
Now we’re going to jump between both the business and the personal here, because you had also recently come out of the closet at around the time, I believe if I’m getting my timing right, that you started this company and that kind of, in your words, kind of blew up your, your life a little bit, you had to reorganize your life and you’re starting a business. So can you just kind of reflect on that and how that is? Yeah. You know, you know, that kind of tumultuous time was for you.
Tony Lillios: 12:31
Yeah. You nailed the timing on the head. So a year into starting the business, and it was somewhat perpetuated by the fact that we had an AOL account. And I noticed that there were all these chat rooms, members created chat rooms on AOL and I was like, whoa, what are all these M for M rooms, M for M San Francisco, M for m la. And I was like, oh my gosh, these are gay chat rooms.
And so I wasn’t closeted at that point. I wasn’t, I just didn’t have any models of what Gay looked like. To me. That felt like I connected dots. I just was like, not me.
I was happily in a relationship. And then after obsessively spending way too much time in these chat rooms, I realized, oh, there’s something here for me. Like, that’s not. Yeah, it’s not as I thought it was. And so starting a business is pretty disruptive.
You’re, you know, you’re not making money. All your money is being spent. So you’re growing this business and it’s feeling good. But we’re not talking, we’re not putting money in our pocket. And then this is like oh, whoa.
Like blowing up a five year relationship with my girlfriend that I was going to marry and have kids and have a white picket fence. And, you know, like, wow, you know, that was really disruptive. And then also feeling like I couldn’t really be out. This is 96, 97. I didn’t feel like the world was ready to.
It wasn’t super accepting as I find it way more now.
John Corcoran: 14:00
It’s interesting to say that because San Francisco, you know, we both have lived in the Bay area. I live in the Bay area. I mean, historically it has been a refuge for gays and lesbians.
Tony Lillios: 14:09
Absolutely. And in certain pockets. And so here I am and EO, I joined EO, I think, in 97. And, you know, I didn’t see any gay people around me. And so it wasn’t as accepting as you say it might be.
There wasn’t representation conspicuously at least. And so I felt very alone, you know. And so I was very closeted in the EO community for a long time because I just I mean, we barely even had women there. It was just that, even though there’s diversity, it was just like this world that I kind of really was thriving in, in EO, it didn’t feel like a really kind of welcoming, diverse place.
John Corcoran: 14:49
And a bit of a good old boys club kind of thing. Absolutely.
Tony Lillios: 14:52
And just from I mean, just, you know, the kind of locker room comments that are being thrown around, you’re like, ooh, that one almost hit me. I’ll just like, I’ll just step back here. You know. Right. And no real harm meant by those.
But, you know, just just noticing this, this feels frothy and and so it was a turbulent time with, like, without a doubt, the hardest time for me I’ve ever been through. Yeah. Where I viscerally like, I’ve been through things that are hard. But like, I could just. My gut was like physically, my body was just like, really not feeling well for about a year or two and all of that.
John Corcoran: 15:31
And when you say that it was, it was hard because you were not living who you weren’t. You weren’t presenting to the world who you were on the inside. Is that what you mean?
Tony Lillios: 15:41
No, that sounds like a nice picture. Talking about it in reverse. The experience of it is it feels like, I don’t know, I just have the trash compactor in Star Wars. It’s just like walls are closed. It feels messy, uncontrolled.
I have no idea what I’m doing. I don’t know where I’m going. I have no maps and there’s.
John Corcoran: 16:02
A weird snake thing from. There’s a snake thing.
Tony Lillios: 16:04
It’s gonna freaking bite me. That’s so freaky. Yeah, I’m just like, I don’t know what I’m doing, you know? And so you’re just. You’re lost is like an understatement.
It’s just because in some ways, like, you’re killing it. In some ways, business was like taking off and, like, you know, my life is really together, but in other ways, you’re like, what am I doing here? Like, what is going on? Yeah. And also coming out and not being closeted.
I think closeted and coming out is one experience not realizing you’re gay. And then suddenly you turn around and it’s like, boom. That’s like, you know, I’m not 16 years old. I’m 27. That’s a very different experience.
I’m not alone in that experience. But we don’t have any.
John Corcoran: 16:52
Happened to a good friend of ours, a neighbor who was in a long term marriage. And, you know, it’s a little difficult for me to understand. Maybe you can help unpack that. Like how is it you can be 27 years old? And in the case of our neighbor, she was early 40s, you know, I mean, how do you think that was?
Was it part of your upbringing? Was it just a part of your psyche that you kind of suppressed or both?
Tony Lillios: 17:17
And suppressed it, or also didn’t wasn’t able to connect it, to make meaning out of it. And so this is where, like when I was young, gay was like Liberace and Elton John. Yeah. So like we have like Pete Buttigieg or I mean, it’s just like it’s crazy in my mind. We have a gay candidate for president like that.
You’re like, yeah, whatever. But like when you’re inside of this and you’re kind of tracking lagging a little bit of remembering what it was like in the 90s and the 80s. Right. It’s not that I was repressing it. I maybe subconsciously in some ways repressing it, but there were no models.
I went to gay weddings. My girlfriend worked in the hotel hospitality industry. I went to gay weddings with her, and nothing about that was like, oh, these are my people, because they were just not quite my people. And just the diversity of the gay community is n’t readily apparent to me, and I just didn’t see my place. So it’s kind of a double whammy.
It’s like one, do I see myself in this community and then am I attracted to that? And it’s weird that you’re like, come on, attraction is kind of fundamental. And I can unwind memories to go, oh, I now see that attraction to that person or that teacher or whatever, like, oh, that’s what that was. But life’s frothy. Like there are a lot of moving balls when you’re that age.
Like, yeah, I, you know, I didn’t stay still long enough to go like, oh, let me pull that thread. You know, it was right of a sideways glance.
John Corcoran: 19:07
I’m going to bounce back to business here. So Spec Design eventually evolves, I believe, and becomes Spec Products. That eventually becomes a business that is creating, you know, cases and things like that for iPhones and laptops. How did that evolution happen?
Tony Lillios: 19:22
Yeah. So when we spun off from the idea, we were like their business model was pretty long in the tooth, kind of like lawyers. What we’re going to do is we’re going to keep cranking. Our billing rates get bigger and bigger. Consultancy.
Yeah. Consultancy. Let’s just have a consultancy. And we’re like, really? That’s the best you got?
You’re going to rent time like it’s the worst.
John Corcoran: 19:42
Yeah.
Tony Lillios: 19:43
I was like, this, this is all you’ve got, you guys. We’re like, I hated it. We think we can do better. And so we started a design consultancy and we immediately called it The Dark Side. It was completely a means to an end, and we literally would refer to it as the dark side.
Time and again it is like that, because it was too easy. It was like, ooh, insta money, you know, like it was kind of like, ooh, you know, get your fix. But we invested in starting other businesses. So from out of spec product design, we started four other businesses. One business is spec products, which is the case company.
So there were two companies named spec at the same time. There still are. And so what happened with us is we were doing work for companies like Dell and a lot of laptop stuff, Dell and Apple, and we realized that we were putting a lot of effort into designing. Making sure the core product was coming out on time, killing it was beautiful, was awesome. And they’d spend some they’d have aspirations to design good accessories with it.
But really, like in pecking order, the accessory was not as critical at launch.
John Corcoran: 20:54
We’re talking about the early 2000 era here, so we’re actually heading into the heyday of consumer products. And, you know, the iPhone isn’t even out. I think you at least looked at your LinkedIn here. iPod is it. Yeah.
So I’m looking at your LinkedIn here, and it looks like spec products started around 2001, which is when the iPod ended up coming out. What was it like when each of these products kind of came out? Were you like, oh, this is a huge opportunity for us to create. Yeah.
Tony Lillios: 21:20
So once our first big case. So we invented the hard case category. So people were making leather cases since we had phones, but phones were free or cheap at first. Then they started getting more expensive and we got these rubberized cases. You know, these kinds of elastomeric cases.
But there’s more sunk. There’s more upfront cost. When you do hard tooling, when you make something plastic. And so you want a form factor, a shape of the core product to be kind of standard, it needs to be a big enough product and a product that’s going to stay in that shape for some amount of time, if it’s going to move at all. That’s a problem.
So the Motorola Razr had a $200 plus flip phone that that format was, we felt was stationary enough. So our first hard cases were for the Motorola Flip phone. iPod comes out, we start making them for the iPod and then all kinds of accessories. And we were the cheese stands alone. At first we were the only ones there with other people in terms of soft goods like leather cases and elastomeric cases.
But we were the only hard case company at first, and it afforded us all kinds of opportunities that the other folks, you know, couldn’t do. And it just established us as a market leader. We were kind of early in that market. People kind of associated us with Apple, and people even thought we were owned by Apple for a long time because we were just always there. One of our big moments was, I don’t know if you remember Antennagate, there was a.
John Corcoran: 22:58
Point.
Tony Lillios: 22:58
Where the iPhone four, if you put your finger across this kind of band.
John Corcoran: 23:02
Right, you could block the phone signal or something like some particular spot. And they discovered this after launching it. Right. So yeah. Exactly.
Tony Lillios: 23:09
So the response was to pick one of five cases for free so that you cover up the metal. And so we were two of the five cases. Oh wow. And so that is that.
John Corcoran: 23:20
Apple basically was like a bulk purchase from you basically.
Tony Lillios: 23:23
Absolutely massive. of and credibility like we are, you know, now 40% of the market and then everybody’s seeing our case out there. So then they’re like, oh, that’s the company to do. So that was definitely a hockey stick moment for us where we were cruising. But that was like not even a hockey stick.
It was a quantum leap. There was just like a chunk like, oh, we’re playing it now, a different level now.
John Corcoran: 23:48
There can be a flip side to that coin, which is, you know, your eggs are all in one basket with one company and they could own you or they can force you to drive down your margins. Did you ever experience that during this period?
Tony Lillios: 24:01
Yes, but we had other distribution channels. So Apple once allowed the phone to be sold by AT&T, then other carriers, those guys were way less sophisticated on how to sell accessories. And so there was a huge hole for us to step into. So we would get better margins. We could work with AT&T.
They had way more stores than Apple and we could work with them in terms of merchandising and pricing and, you know, scripts and, you know, training salespeople. And so at first AT&T and then all the carriers really became like our primo market. Yeah, we eventually pulled out of the Apple Store. So even though that core product was super important to us being in the Apple Store, the margins started to not make sense anymore. And our brand was strong enough that we didn’t need it.
No one was missing us by not being in the store.
John Corcoran: 25:04
I want to ask you about the company itself. You had another competitor that was kind of like the big competitor out there, but they were a little bit more kind of on the straight and narrow kind of basic boring products. And one of the things you did with spec is embracing more, not just more colorful products, but also as a company embracing a more colorful team and allowing people to kind of be themselves. And it is a really interesting demonstration of a company that tries that both kind of walks the walk and talks the talk and kind of who they are to the world is who you were internally, or at least that was the goal. So talk a little bit about that, the intention behind that.
Tony Lillios: 25:44
Yeah. So it’s easier to tell a story backwards that this is what we intended to do. It was kind of just in our DNA. We were a very diverse crowd. We were very colorful.
And we really, you know, one of my core values is to bring out the color. And we just did that inside and then out with our products. So it wasn’t necessarily an overly calculated move. In the beginning it was somewhat like just well, this just our brand was kind of who we are. You know, it’s just kind of like, you know, you bleed it, you sweat it.
It just is. And then realizing like, oh, in a marketplace, that’s how we get perceived. You know, where people I still meet to this day are like, oh, you started Spec and they just have this warm kind of like, God, I love every phone I’ve ever had. Had a Spec case on it. And they say it in this loving kind of meaningful way.
Not like I’m not saying it’s like over the moon, but it’s definitely not like, oh yeah, I know that company. Like, oh yeah, you know, Belkin, I’ve had a Belkin, blah, blah blah. You know, it means something to people and that it means something to us. And so that and how.
John Corcoran: 27:01
Did that go with the idea of establishing a company culture and attracting people to work for you?
Tony Lillios: 27:06
Yeah, we really got people who were comfortable fully being themselves. So it was a place where people came alive. So it wasn’t like they had to shrink themselves down to show up in a box at work to do the thing that they were asked to do. They actually kind of stepped in and people were kind of alive and thriving within the company. And it became an attractive place to work.
It’s like, gosh, you could feel the energy. I mean, you just walk in the room and it’s just physically the energy of the individuals. It just was like a blooming, blossoming garden, you know, it was just like, wow, what is going on in here? You’d feel it in the first interview. And so that just kind of attracted more of that.
So much so that when we went through our first significant layoff, it was somewhere like 15, 20%. There was kind of a pullback. And we laid off people. We had people that were thanking me because they were laid off, that were thanking me for the sake of the company making the hard choice to lay them off because they cared so much about this culture and the company. Yeah, I was like, bawling because I’m like, feeling like the schmuck to like, be doing this.
But to have people reflect back that we had been creating something that meant something to even the people as they walk out the door. That meant a lot.
John Corcoran: 28:40
Yeah. I mentioned in the preview that there are these different moments in your life where you kind of go into uncharted waters, and one of them was around 2010, so you end up and I may be mixing up the timeline here, but the company had you had a couple of, I think, acquisitions by private equity. A first one and then a second one. And you ended up moving from Palo Alto to Tahoe, which as a gay man is, is a little bit definitely uncharted. Tahoe is not really known as a Gay Mecca.
Gay Mecca at all. Right. Exactly. So. And then you end up having children after that?
Yeah, we’ll get to that. But first, what inspired that move to the mountains?
Tony Lillios: 29:26
Yeah. So without a doubt, when I’m moving from San Francisco, like the Castro in San Francisco to Lake Tahoe, friends were like, what are you doing? Like, you’re like, it just didn’t make sense to anybody. But it felt very natural to me. Natural in that I had to do it.
It was two front, two steps. One, I was training to do a big expedition to go to Bhutan. So we were doing an unprecedented crossing of the country. And I wasn’t naturally or historically someone who was like doing this kind of stuff. So I moved to Tahoe.
Part of the move was I wanted a year with woods in my backyard that I could train on the regular With ease so that I would show up at this expedition as a leader for other people. With some kind of competence and fitness. The other side of it was I knew I wanted to start a family, and there were so many shiny things, people and activities in San Francisco. I could just get busy dating and doing. I mean, it’s like it’s an awesome city.
There’s tons of things to do.
John Corcoran: 30:37
Restaurants, there’s activities. Yeah, it’s.
Tony Lillios: 30:39
Just like my calendar can get packed super easily. So I actually had to remove myself. I chose to remove myself from that to kind of leave space to actually work on the bigger thing of starting a family. Didn’t fully have that figured out of what that was going to look like, but I knew it was important to me, and I needed to kind of take it down a notch. Space on the calendar, space in my life. Space in my house.
I lived in a one bedroom house. Like, that wasn’t going to happen. Like there was. I looked into adopting at first, and they’re like, every kid you adopt needs their own bedroom. I was like, I barely have a bedroom.
You know, like, so like, so this isn’t going to work. So that all kind of started this kind of, you know, movement towards Tahoe. Which opened up so much for me.
John Corcoran: 31:29
And, this actually became a film crossing Bhutan. But what inspired that? Why did you decide you wanted to be a part of that and why? Bhutan.
Tony Lillios: 31:39
The expedition leader, a woman, Terry Schneider. She’d been a coach. He’s a good friend. She literally called me one day and was like, how’d you like to lead an expedition across Bhutan? I’m like, when Terry calls you and asks you a question like that, you kind of have to say yes.
I mean, there’s no. And then you figure out how to do it. And so I’d been wanting to go to Bhutan for a while. There was a lot there that I’d been curious about but didn’t quite understand. And I’ve been waiting to go there in a meaningful way, and this felt like a super meaningful way.
Yeah. As we started unpack, it started working with the government to make this super special thing happen. Then it became, oh, we need to make a film for this. Like, there’s no way we can selfishly just have this experience and not kind of document to some degree there. And we were also chartered with elevating and really starting a culture of sport in Bhutan, which is brand new.
And so just recently, having the Bhutanese marathon runner kind of running the Olympics was an emotional moment. She had run the Bhutan International Marathon that we had started a couple times. And yeah, we just that was part of it was let’s go do this, go deep in the country and then figure out as athletes how we can bring that kind of elevation to a country that doesn’t really have a sporting culture.
John Corcoran: 33:10
So I guess in a sense, after doing that, coming back to Tahoe and then saying, as a gay man without a partner, I’m going to go adopt a child, doesn’t seem so crazy, does it? Totally.
Tony Lillios: 33:22
And then I even further went, I’m not going to adopt. I wanted to take matters into my own hands. So I ended up going down the surrogacy route and it felt super crazy. Just like a fast forward, a little quick anecdote is like I showed Richard Branson how he’d never mountain bikes before and he was in Tahoe. So I took him mountain biking about a year and a half ago, and in the early part of the ride I told him I, you know, I started a family of my own, you know, I’m a gay, single, gay man, blah, blah, blah, blah, blah.
Hours later, we’re at lunch and he turns to me and goes, did you say you had kids on your own? Like, he was like he was still, like, grinding on this, like simmering. Simmering like. Jesus. You’re crazy.
Like, gives you this big high five, you know. But it did feel like there was so much of my life that I felt like I had kind of stepped through and stepped into things that were like, oh my gosh, I can’t, I can’t, but I’m doing it, so I guess I can and.
John Corcoran: 34:26
Well, what? Well, one of those is this subtle thing you just kind of glossed over, which was meeting like probably the world’s most famous entrepreneur. So how did you even connect? You just kind of dropped when I met Richard Branson, but how did that come about?
Tony Lillios: 34:39
There are lots of like, it’s really like an embarrassment of riches in situations like that. A friend of mine is an EO, is an events coordinator and was organizing an event where he was speaking here in Reno and asked me for some suggestions of things he might do, and one of them was mountain biking. And one of the things I offered was mountain biking. And I have a friend who’s a 4 or 5 time national champion. And so I was like, she should go take him out biking.
Turns out she was busy. She had pre commitments. He chose mountain biking. And I was like, I think I’m good enough, like the guy. And it’s interesting because it’s kind of in line with his values.
The guy does not look for anything premium. He knows what’s enough and develops from there. So like his staff or business models or he’s not kind of optimizing constantly. He’s like he’s sorting for culture and kind of building from there. Yeah.
Which I now know. And so in hindsight, I didn’t know this at the time, but I was like.
John Corcoran: 35:48
You’re thinking it needs to be perfect. It needs to be the best bike ever. It needs to be the best route ever.
Tony Lillios: 35:53
Yeah, exactly. Stressing about all that stuff and like, okay, I’m going to shuttle him to the start and blah, blah, blah. He’s like, I’m not going to get a shuttle. I’ll bike up to the start. I’m like, it’s going to be an hour, an hour and a half, like straight uphill in the smoke at elevation.
You live at sea level. Dude, you sure you don’t want the van here? Do you want to get in this van? He’s like, no way. And he went up.
Well, yeah. He’s still yeah. He’s like, I’m gonna. I came here to ride. What do you think?
John Corcoran: 36:19
Amazing. Amazing.
Tony Lillios: 36:20
So. Yeah. So. But it’s not like it is amazing. And it’s led to, like, you know, I went to Bhutan with him last year.
I’m going to Dubai with him in a small group in a couple of months. And so it’s unlocked these things. But it’s kind of how they kind of build on each other. So it’s not like this anecdotal thing that just came out of nowhere. It’s because I’ve been living a life of stepping into this uncharted kind of territory constantly.
So it becomes kind of a practice like I don’t. And it’s not that it’s easy. It’s just like, oh, there’s tension. I don’t have self-doubt or negative self-talk or, you know, all this stuff, and then what do I do with that? How do I then say yes and or how?
What do I like? Oh, I’m going to Bhutan or lead an expedition. Well, I might actually need to train for a year. So it’s not just like, woo hoo, let’s go do this. It’s like it gets followed up by action that leads to, like, more likelihood of success.
Yeah.
John Corcoran: 37:28
But by the way, super similar to Richard Branson himself because he’s kind of the same way. Just just tackle stuff that, you know, previously never thought was possible. And he’s done it time and time again.
Tony Lillios: 37:39
Fails a shit ton.
John Corcoran: 37:40
And he does for sure.
Tony Lillios: 37:42
Yeah. And also the thing that we connect on is he doesn’t just do that professionally, but personally he is still pushing physical boundaries. That’s part of what this trip is. Every year a small group of us, like 2025 of us, do a physical challenge somewhere on the planet. And I mean, it’s pushing people.
You know, one guy ended up in the hospital last year, almost dying. Like it’s, you know, as his son was airlifted off of the, you know, on top of a mountain because he almost was dying a couple years ago at one of these. And so he’s not he. He gets that pushing yourself physically and pushing yourself socially and pushing yourself business wise. It’s like all it’s part of the view is.
John Corcoran: 38:24
I haven’t been to his island, but I’ve interviewed a number of people that have been there and they’ve said that oftentimes he is as engaged as everyone. When people are meeting on the island, bring smart people in. He’s taking notes, he’s asking questions. He’s directing different team members to follow up on different ideas. So it’s really amazing to see.
Super curious. I think he’s super mid 70s by now or some early 70s for. Yeah, still going, still going. Love the energy. Yeah.
Let’s talk about your I think it was your daughter was your oldest.
Tony Lillios: 38:55
Yep.
John Corcoran: 38:56
Okay. And you end up having another one after that. But you know I know there was a moment I think it was when your daughter got to about age one where you look back and you said, oh my God, I’m doing this. I’ve, I’ve made it. I can, I can actually have the ability to do this.
So talk a little bit about that.
Tony Lillios: 39:13
Totally. And I think we all have that when we step through, you know, into uncharted territory. There’s that moment where you’re like, oh, I’m actually an Iron man now. I’ve actually done 13 of them, like, I, I do this thing like it’s. And so yeah, it was on our first birthday.
It was a friend of mine, actually my ex-girlfriend, the one that I broke up with when I came out, she sent me a text to something like that. Happy birthday. And you’re doing it and. Yeah. Sometimes you get so kind of occupied with just, like, one foot in front of the other, you know, like just doing the things and you kind of stop to it.
It’s helpful to stop and look back and go, wow, where have I come? Where what what where? Where have I arrived? In the space I am and where am I going? Like, it’s just taking stock, you know?
It’s like going on a bike ride, you know? Right. Riding a mount Tam from San Francisco, like you get to Mount Tam and you look back and you’re like, I started over there like I never did. If you told me I had to do that, I’d be like, no way. But somehow you just do the things and then you’re like, oh my gosh, I’m doing it.
So it’s that kind of sensation where I was like, wow. I’m actually like, I’m like, I’m, I’m, I’m doing this thing.
John Corcoran: 40:31
And you mentioned doing Ironmans, but you actually had not been, I believe, all that athletic or didn’t consider yourself an athlete growing up. How did you get into doing Ironmans?
Tony Lillios: 40:44
Yeah, just little by little I was dabbling with it with other folks at Spec, there was a group of us where we, 40 out of 60, challenged ourselves to do a half Ironman in six months time. I had already done a half, so I was like, wow, I was really inspired by these guys doing this, half signing up for this half. But I was like, I feel like a chump if I just put my name on the list, like, I’ll do it with them, but what’s my bar like? Where’s my similar discomfort? That’s when I signed up for my first Ironman.
The only one I could find that was open was in Western Australia, which was in Boston. I was literally like on the other side of the planet, like drilling a hole through and like, that’s where the race was going to be in six months from then. And I really was convinced I couldn’t do this thing. I was like, I’m going to do the motions. I hired Terry, the future expedition leader of Bhutan, as a coach.
And just like I just did the thing, just put my head down, like try to be a good student, just like, do the things she said I know better. Like, just if you do the things, you’re going to be great. I’m like, okay, I’ll do the things. And when you cross the finish line of Ironman, it’s a tradition where they say, Tony Lilius, you are an ironman. And I can still remember.
I remember I was like two thirds to the right, looking up at the star. I can remember that moment so well. It’s like chicken skin when I think about it. And I remember that sense of like, well, that’s a label I cannot, I can’t discount or dismiss that anymore. Like it’s like, oh shucks, I got lucky in business.
The iPod, I had great partners. Like, like I have I I’ll speak for myself like I dismiss and diminish stuff all the time. But like when you do an Iron Man, you’re like, you can’t do that. Like, it’s like you have to own it and you’re like, it’s like a stamp. You’re like, now I got, you know, it’s a tattoo.
That’s why some people get tattoos. And so it started this phrase. I can remember the phrase in my head at that moment too, was like, what else am I convincing myself I cannot do? What else am I convincing? I’m actively working to like, push down that no, no, no, you can’t do that.
And that’s where starting a family like I can draw a line to doing that first Iron Man straight back from that moment straight forward to starting a family on my own like I was. I had all these reasons and we’re not going to pack it all, but all these stories of why I couldn’t do that gay man by myself, you know, not good for kids older and but broke that down. And I’m so glad I stepped through that. I’m so happy and proud and love my life as a dad. All right.
John Corcoran: 43:23
We’re picking back up and we’re wearing different attire. If you’re watching this on video, it’s because we had a couple of day break between this, but we’re picking back up. And Tony, you were saying that, you know, you had all these different reasons in your head why you couldn’t do certain things. You were a gay man. You’re single, you live in Lake Tahoe.
You know, that kind of held you back from doing certain things in life. And then as you did these physical competitions, as you did Iron Man’s, as you had these achievements, it made you realize there was so much more that you could do.
Tony Lillios: 43:58
Absolutely. Yeah. And when I crossed that first Ironman finish line, there was this announcement. You know, Tony, you are an Ironman. Yeah.
And there was a moment there where I just felt like that was a label. Now that I was convinced six months ago that I, you know, that would never happen. Here I am, this guy that’s living and being this thing now that I wasn’t. And so that did start to crumble and start to erode all that narrative in my head about what stories I am telling myself that I can’t do? And I continued to march forward and do things in the physical domain to kind of break down things.
I qualified for Boston four months after that Boston Marathon. Yeah.
John Corcoran: 44:48
Famously, one of the most competitive race marathons to qualify for.
Tony Lillios: 44:52
Yeah. I mean, and I was like, I’m not a runner. Like, oh, but maybe I am a runner. Like that was such a hard baked story about me not being a runner. And you know, I’m qualifying for Boston.
Dude, you gotta like, take a little bit like no one else ran the marathon like that was you. And so I continue to do that and start to erode on these stories. And some of these stories are internal narratives, like a belief of what I thought. But there were cultural narratives too. So being a parent, a single gay parent, there was prop eight was kind of in discussion in California at this point of whether or not gay marriage should be allowed or not, which.
John Corcoran: 45:36
Passed in 22,008. So this was before 2008 that you’re having these thoughts.
Tony Lillios: 45:43
Yeah. So it’s in the milieu and the.
John Corcoran: 45:45
Prop eight was was the the backlash that banned gay marriage in California before the U.S. Supreme Court overturned it.
Tony Lillios: 45:52
Exactly. And so the timing. Exactly when it is allowed or not allowed is actually not as relevant for me. The point is, it’s a conversation. There was a significant population.
There were forces at play saying you shouldn’t be married and you shouldn’t have kids and so on.
John Corcoran: 46:12
And it passed on the same night that Barack Obama was elected in 2008. And it was you know, I remember because I live here in the San Francisco Bay area, how devastating it was for the LGBTQ community that that passed at the time.
Tony Lillios: 46:28
Yeah, absolutely. And so you can get righteous about it and go, that’s wrong. And, you know, I don’t believe it. And it should be x, y, z. But the way I live is like if there are voices saying it’s not a lot of voices, a choir of voices saying, you shouldn’t be doing this.
Part of me wonders. Like maybe they’re right, you know? Maybe some part of that is right. And so it’s breaking down those stories of why are they singing that so loudly, and why are they so, like, aggressive about it? Like, really it’s like you don’t get gay married.
Like, why does my marriage or my parenthood matter so much to you? Like, it’s a little like, geez. Like, okay, I poked the bear. Right? So it was breaking that down.
It was part of the process of being able to step into parenthood by myself as a gay parent.
John Corcoran: 47:30
And one of the things you did was you were the only person to swim across and back Crater Lake, 11 miles without any assistance. And there weren’t also weren’t any boats allowed in the lake. So you had to do it without any kind of support.
Tony Lillios: 47:43
Yeah. So unassisted swimming is a term that’s used in general. Most swims are unassisted. So unassisted just means no one. You didn’t draft off of something.
The boat stayed behind you. But I always thought that term was a little misleading because unassisted is like, dude, there’s a boat with food and people and rescues and you know, that doesn’t really that doesn’t really sound like unassisted to me. So what I did was what I called unassisted. And it’s now one of the terms that’s used to describe it is called wild swimming, which is there’s nobody around like you are the only person doing that. And if you kind of look up wild swimming.
My swim of Crater Lake is considered one of the original big wild swims. Like it’s there have been wild swims since then, but it’s kind of one of the, you know, first points of, you know, that and it’s very it’s a whole different game. There’s no no one who knows I’m out there knowing there’s no safety net at all. Yeah. Which was you know, it felt like all the preparation going into it was there and then.
But there’s still those questions like, did I forget something? Did I miss something? Am I, you know, am I really dumb? Is there a good reason no one’s done this before? And I can still remember jumping off that edge and just very quickly as you swim off, it’s just like the cliff just drops so fast and you’re just a deep kind of electric blue water.
And it felt like I was going to the moon, like it was my version of, like, I have no one’s ever done this, so I don’t know how this goes, you know, am I like, did I not? Oh, it’s a whirlpool in the middle and you’re going to get stuck, you know. Yeah. You know, like I don’t actually do.
John Corcoran: 49:35
You said one of the only fears is that you’re going to hit the old man of the lake. Which Crater Lake has got this? Well, you tell it this crazy story of this bobbing log that has been there for, I think, 100 years or something. It just floats around the lake.
Tony Lillios: 49:50
Exactly. Yeah. And that’s one of my, like, fears is you can be very kind of zenned out and swimming. And but then suddenly this thought is like, oh my gosh, if the old man comes in front of me and I just, like, go headlong into it, like, and again, if I hurt myself, there’s no one that’s going to come and save me. I have to.
John Corcoran: 50:12
Say, the odds of that are pretty astronomical. Right. Exactly right.
Tony Lillios: 50:17
Yeah. Same thing with sharks. You know, it’s kind of that’s like another one of those, like, you’re not going to get attacked by a shark. And that’s one of the things I kind of coach other people in swimming or otherwise. It’s like I don’t live in fear or worry much.
It’s like if you’re actually concerned, you’re going to get attacked by a shark, then if I speak in first person, if I’m actually concerned, I’ll get out of the water or I’ll say, it’s like my brain will go. Yeah, that could happen. But it’s not going to happen to me today. And I just keep swimming so I don’t sit. I don’t like that limbo state of like, maybe should I could and it’s like, no, decide if you really think it’s a material concern, then make a decision to put yourself in safety or like stop worrying and just do the swim, because worrying is not going to reduce the chances, it just makes it so much more unpleasant.
And so I catch myself much more. And that’s part of the practice of doing this. Open water swimming and all these things is I have a practice now of not really being in worry much. I actually bailed on a swim within the month, where I was not feeling good about the way the race was running, the weather, the visibility. There wasn’t enough support and I was like, this feels unsafe.
People around me are really stressed. I don’t want to contribute to this. I’m not feeling good. I turned around and got out of the water. I was like, I don’t, I don’t I’m not feeling it today.
John Corcoran: 51:43
So trusting your gut on that. Yeah I want to get to how this comes to play in your What You Do now which is supporting other entrepreneurs. But before we get to that kind of a key milestone, you end up selling your company, which in many ways is emerging into uncharted waters for you. And you did an interesting thing when you sold your company. You sat down with each of the key team members who were getting significant money, I guess a share of the sale price.
And you had a meeting with each of them. Tell us about that.
Tony Lillios: 52:16
Yeah. So anyone with six figures or above, we had a 20 to 30 minute meeting all day long. We had a kind of special place offsite. We scheduled it rail to rail. And they did.
John Corcoran: 52:32
Know what was coming? Did they come into the meeting or did they think they’re getting fired or what? Did they know their expectations?
Tony Lillios: 52:38
Everyone knew the company was selling that day, though it was very public. Okay. And they didn’t necessarily know they were going to receive a check, but they knew that we wanted to have a one on one meeting. And I’m sure there was enough chatter of like, oh, it’s those people that are getting, you know, it’s the higher ranking people that are having the conversation.
John Corcoran: 52:56
And this was discretionary. They didn’t have equity. You were just deciding to give them.
Tony Lillios: 52:59
We had what’s called stock appreciation rights. So it was a form of equity but not hard equity. So this and a bit of stock appreciation rights because it’s not hard equity I feel like there’s a degree of trust. You know it’s it’s agreement between you and the employee that when and if and when there’s a watershed, you know, a watershed event which is somewhat qualitative, it’s not quantitative. That triggers this event in which they’re entitled to a bunch of these phantom shares, these stock appreciation rights in which they’ll be rewarded.
And I felt like it was a little bit of convincing people and trusting them, trusting us with these contracts, especially because it was kind of new back then. And it felt so great to like, make good on that. Like I wasn’t going to just let it be a wire transfer. I was like, we are good guys and we’re doing the thing, you know?
John Corcoran: 53:55
How emotional was that, that experience for everyone.
Tony Lillios: 53:59
It was super emotional, you know, just share. We would share how this is changing our lives. We’d ask, you know, if they’re wanting to share how they think this is going to shift in their life and what this means for the company moving forward. So we yeah. And it was just like back to back and the variety, you know, some people are like childless and young.
And this means x y z you know, like, oh, I’m going to publish books and I’m going to, you know, put a down payment where other people are like, oh, I’m paying for college, or I can take care of my parents or like, oh my gosh, I, you know, it just it became. Came. Yeah, just like a cornucopia of things that people were going to use it for, which was really it was so meaningful because we’re like, this is meaningful money, people. This isn’t just like a bonus. This was like game changer money.
And yeah, it was wild. And then at the end of it, we finished up the last person and my business partner Ryan turns to me and he goes, let’s go ring the bell. And I was like, oh no, you didn’t. He remembered a story. When we started the company, we used to go to this English pub called the Rose and Crown, and there was a bell there that if you rang the bell, the tradition was that you had to buy the whole house.
A round of drinks.
John Corcoran: 55:27
Okay.
Tony Lillios: 55:28
And I told him once, probably 10 to 12 years prior, someday when we’re rich, I’m going to come in here and ring that bell. He squirreled away this little story for years, and he was like, let’s go ring that bell. And I was like, oh, yeah. And on the way there, I’m calling my brother, calling my friends. Like, we’re just like calling everyone.
And we show up at Rose and Crown and it’s a beer tasting brewery night. It’s stacked. It’s like, so I am like, so stressed out. I’m like, oh my gosh, it’s gonna be thousands and thousands of dollars. And you’re in Palo.
John Corcoran: 56:06
Alto, by the way. So there’s probably some other well-heeled individuals in there that are like, nah, no big deal.
Tony Lillios: 56:13
It was $687.
John Corcoran: 56:15
I was the bill. The bill was $687.
Tony Lillios: 56:17
Yeah, totally. And because you write your name and then how much you spent. Oh, on the wall, there’s a list of everybody’s name.
John Corcoran: 56:24
Who’s rung the.
Tony Lillios: 56:24
Bell. Yeah. I just assumed it was going to be thousands and thousands. And I was like.
John Corcoran: 56:29
Somewhere in there is Zuckerberg like, yeah, $17,000 for something like that.
John Corcoran: 56:35
Yeah. That’s cool. So now you have moved on from that and, you know, become a business coach if that’s the term that you like to use. Yeah.
Tony Lillios: 56:45
Leadership coaching is what I use.
John Corcoran: 56:47
Now how did you decide that that was the next chapter for you. At what point was it after you sold the company you decided that or was it before it was kind.
Tony Lillios: 56:54
In the middle, because the selling of the company was like a multi-stage. We had private equity. Then we sold the whole kit and caboodle. So there’s kind of a phase thing. And being a coach also involved me going back to school first.
So I went to school in San Francisco, to New Ventures West to get coached, to learn to be an integral coach. What happened was I was a client of a company called staging out of Dallas about 11, 12 years ago, 11 years ago, and it’s a one year program that involved coaching. And I got this experience of, for the first time, being really coached, not working with a consultant. So for me, consultants like to have an experience, have a knowledge base or a skill that they’re doing or they’re teaching you how to do. So it’s very kind of like tactical, whereas coaching is much more qualitative.
And, you know, I like to say coaches, the answers lie with a client and a coach. A coach is helping kind of bring out solutions that are coming from a client. We’re not telling what clients should do. And so it was my first experience of real coaching. And I was like, oh my God, this guy who doesn’t know anything about my business was really skillfully coaching me as a person that happened to be a leader of a company.
And I just was like, man, I could do that. Because then like, once you learn that skill, that is something that’s translatable to anyone. You don’t actually have to, like, know their business and even like more recently, I mean, now this is like 3 or 4 years ago, there was a moment of flash in the pan moment where I was being considered a Coach Zuckerberg. Funny, you mentioned him and it was like, barely moved. Like I was right at the front door and didn’t get far.
But the point was, I felt very confident that like, oh, do I know how to run his business? Hell no. Do I know that? Do I have something of value as a coach that I could bring to the table to have him grow 100%?
John Corcoran: 59:02
Like, the funny thing is, he’s actually gotten into more physical competition and things in recent years.
Tony Lillios: 59:08
Absolutely. So this was right before that. So. Right.
John Corcoran: 59:11
Sorry, sorry I hit the wrong button there. Okay. Keep going.
Tony Lillios: 59:14
Right before that all happened, a friend of mine is a friend of his and he was considering doing his first Ironman. So I was kind of through my friend talking to him about what that looked like to kind of step into that domain, and it sounded like it was too big of a thing for him to step into? But then, yeah, after that didn’t happen, that’s when the jiu jitsu stuff started happening. And I don’t know if that was coach driven or personally driven or brand driven. Like I, you know, I’m not sure where that all came from, but I was happy to see that I was like, this guy could use to, you know, to step into some power and, you know, have an embodied experience of what that looks like.
Yeah. So yeah, I was glad to see him do that.
John Corcoran: 59:56
And has that been a critical component of your coaching is working with leaders that also want to embrace that physical side or run ironmans or marathons?
Tony Lillios: 1:00:05
It doesn’t always have to happen, but I usually like to include some aspect of it depending on the client. So it’s not like, oh, all clients run ten K’s or Ironmans. It’s usually more specific. Like I have a client right now doing Krav Maga, which is kind of a form, and specifically that form of martial art. There’s a reason I didn’t take jiu jitsu or aikido or.
And so with clients, I like them to have embodied experiences, like a physical experience of something that they’re working on. Because just like I was saying before, like how you practice in these other domains rolls into all the other domains. So it’s really helpful. Like one of the analogies I use is like, you know, if you’re if you’re doing a dumbbell curl and I do it right here on my desk, or I do it in my car, or I do it at a gym, like my bicep is like, thank you. Like you’re doing the bicep curl.
It doesn’t really matter where you do it. Your bicep is developing. And so these skills of learning to step into power or you know how to downregulate or, you know, whatever the thing that you’re working on, practicing at home with your kids, with your family, you know, with your coworkers, with your boss, like it doesn’t matter. Like you’re in the practice and so Practicing can happen in a lot of domains, and in fact, it’s easier for sometimes people to practice in domains that don’t have as high stakes, like not with their boss or not in a public forum. So I’m like, of course, let’s practice over here.
But then as they get more skillful and used to it and have an embodied experience, it kind of almost naturally spills over into areas that are kind of higher stakes and people are kind of afraid to, but once they get some confidence and some kind of skillfulness with a new way of showing up in the world, they’re more likely to show up that way.
John Corcoran: 1:01:59
Yeah, Tony, this has been great. I’d love to wrap up with my last question, which is my gratitude question. I’m a big fan of giving people the space to acknowledge anyone, especially peers or contemporaries or mentors, especially mentors who are still in your life and just kind of thank them for being a part of your life, giving them a shout out. So who would you want to acknowledge?
Tony Lillios: 1:02:25
Yeah. Chip Conley has been this character in my life, throughout my life. When I first joined EOE, he was a speaker. He wrote his first book, Rebel Rules. He was a speaker at USF, and there was something about him that I really kind of magnetically connected with. I read his book, was really into him, and didn’t see him again for maybe 10 or 15 years.
When I started to do the expedition across Bhutan, I reached out to him through friends. He was so willing to talk to me. He had done a TEDx talk on Bhutan. I wanted to connect with him and learn more. He gave me time.
He gave me connections. CEO of Patagonia for sponsorship and ideas. He was so generous, like out the gate and he didn’t even know me from Adam. And it was so. Yeah, you could feel just this, this generosity in him.
That was just. I didn’t feel like I earned it, and it made me feel like, oh, I was on to something. Like here. Here. I wasn’t really sure.
Are we doing this thing? And his kind of support early on, really unknowing to him really kind of was a backstop and allowed me to kind of step into a more physical domain doing the film, kind of being a coach. And, and then our friendship evolved from that point on, you know, we started doing more and more stuff together. I’ll be down in Santa Fe’s new campus. He’s got a group called the Modern Elder Academy.
He’s built a new campus in Santa Fe. I’ll be down there for his birthday, for his 65th birthday in a couple weeks. And it just felt very privileged to be in his inner circle, both as a friend, as a business mind and just like we kind of wrestle really well together and he’s like, definitely not a peer. Like he’s not just ten years older. He’s just wiser, you know, way beyond ten years and much more experienced.
And I love that he, you know, I wouldn’t. I don’t know if he knows that I would consider him a mentor, but he absolutely has been a mentor at a distance for me for, for many years now.
John Corcoran: 1:04:47
Awesome. Tony, thank you so much for your time. Where can people go to learn more about you and connect with you and reach out?
Tony Lillios: 1:04:53
Yeah. Lillios.Com is where kind of all the stuff feeds out from and that’s being updated as we speak. So Lillios.Com and that’s where you can find out all about me.
John Corcoran: 1:05:04
Excellent. Tony thanks so much. Thanks, John.
Outro: 1:05:09
Thanks for listening to the Smart Business Revolution Podcast. We’ll see you again next time and be sure to click subscribe to get future episodes.