Funeral Faux Pas, Long Term Criminal Minds, and More with Tom Webster

Tom Webster: 00:00:00

I don't know that I really want to get too specific about it, but I do think second marriages are wonderful. I think you're much clearer about what it is that you want and don't want and you spend the time getting to know that person a little bit more.

Danny Brown: 00:00:17

Hi and welcome to Five Random Questions, the show where every question is an adventure. I'm your host Danny Brown, and each week I'll be asking my guests five questions created by a random question generator.

The guest has no idea what the questions are and neither do I, which means this could go either way. So sit back, relax, and let's dive into this week's episode. Today's guest is Tom Webster.

Tom is partner at Sounds Profitable, a collection of media properties that provides industry leading research around podcasts' most pressing questions.

Previously he was Senior Vice President at Edison Research and he's also the co author of the annual Infinite Dial study that looks at the habits and trends of the podcasting industry. He's also a podcast hall of fame inductee. So, Tom with the very, very impressive bio, welcome to 5 Random Questions.

Tom Webster: 00:01:03

Thanks, Danny. And I just want to let you know that I'm terrified, just absolutely terrified of this format, you know, because I like to control everything so.

Danny Brown: 00:01:11

Well, I was going to say, I mean, you're a very. When I've seen you speak and when I've met you, I've spoken to you, you seem a very confident person. So it's interesting to hear.

This is like throwing you a little bit, which is. That's a fun part of this show, I feel.

Tom Webster: 00:01:24

Yeah, I think so. I mean, I enjoy the speaking.

I don't know if it's confidence or not, but you know, it's preparation times, anxiety times, just the number of reps I've had doing it. But I don't know, like, I don't know what you've seeded this random question generator with. So yeah, we're going to find out together.

Danny Brown: 00:01:43

Put little AI prompts in there just to throw you completely. And I'd mentioned, obviously your bio is super impressive, very professional, with lots of achievements over the years.

But for anyone that follows you on Bluesky, that's a complete opposite and super simple where all you do is you mention that you do podcasting stats and jokes and that's pretty much it. So what's your favorite joke about podcasting or stats or favorite joke overall? And this isn't part of the random questions. I'm just curious.

Tom Webster: 00:02:09

Oh yeah, I know about a favorite joke about stats, but something a line That I cite a lot when I see, you know, there's two kinds of research, right? There's research to show and there's research to know. And I try to do a lot of research to know.

There are plenty of people who do research to show they have a preordained idea that they want to quote, unquote, prove, right? And the thing that I will often say about that is that they're using statistics like a drunkard uses a lamppost for support, not illumination.

So there you go. There's some statistics comedy for you, Danny. That's. There's not a lot of that in the world. That might be the only statistics joke I know.

Danny Brown: 00:02:48

That's.

I'm gonna open now with that, you know, if I ever do any speak, I'm gonna open with that and say, hey, it's good enough for Tom, it's good enough for you guys. And speaking. Well, no, not really speaking of jokes as such, but speaking of stepping away from your professional life.

You made me super jealous last week because you got to see legendary UK rock vocalist John Wayt in concert without making me feel even more jealous. How was.

Tom Webster: 00:03:14

Was phenomenal. You know, I think John Waite has never gotten his full due, right?

You know, not to go like too far down memory lane with everybody, but, you know, he had some great songs with the babies, he had some great songs with Bad English, some great songs solo.

But the thing that just kind of blew me away, and I saw him in a fairly small venue was just how great and in the same key and range his voice still is at 73.

And, you know, he closed the show with this bananas version of Whole Lot of Love by Led Zeppelin that Robert Plant could not even do today in that way. And it was just like, I don't know, I just left like so, so full of Joy because for 90 minutes he just sang his face off.

And I don't know anybody who wouldn't have loved that show.

Danny Brown: 00:04:04

Nah.

And I almost wondered if, like the singers from that era, because obviously he was in the Babies in the 70s, then he did his solo stuff and then in Bad English, kind of late 8, mid-90s. I wonder if the singers from that era just have that longer lasting vocal range compared. I'm not putting down any singers today, but I think of.

You mentioned Robert Plant. I think of Steve Perry at Journey.

You know, people like that Anne Wilson of Heart, they still seem to be able to hit these notes and sing these songs when they should just be relaxing in retirement as a pensioner.

Tom Webster: 00:04:34

You would I don't know. I, I, you know, I, I just sort of look at it like they just love it. You know what I mean?

Like, there are probably a lot of people working, like, at insurance companies that when they retire, think, oh, I'm going to become a singer, because that's what I would have rather have done. Well, I think if you have been a rock star, a pop star, or, you know, just a gigging, working vocalist, I. Why would you quit that?

As long as your voice holds out that, you know, I'm very jealous of all that.

Danny Brown: 00:05:00

I hear you. Well, speaking of doing something that you do outside of what you do as a day job, it's time for five random questions, I feel.

Let's get you in this hot seat, Tom, and let's bring up the random question generator. We'll see what comes up here. So let's have a look then. Question number one. Okay, this is a nice easy one. He says to open up the episode.

Question number one, Tom. What are some things that you should not say at a funeral?

Tom Webster: 00:05:30

Oh, some things you should not say at a funeral. Okay. Okay. I think number one would be, is there also. Is there going to be food here? Because I'm, I'm starving. I think that's at the funeral itself.

That's, that's probably not great. I'm happy to see they got what they deserved. Would probably be low on the list. Right. And you know that, that guy. Thank God. Yeah.

Things you should not say at a funeral. That's. Yeah, I'm going to go with that. Couldn't have happened to a better person.

Danny Brown: 00:06:08

Well, I think that it's weird because, like, you say you've got the funeral and then obviously you've got the service, I guess, afterward. So I'm guessing this is on about the funeral. Whether that's the burial or the cremation. I was trying to think of the word for the.

Not burial, the cremation. I mean, have you ever been to, like, without being too morbid, but have you ever been to.

If you know where someone said something that you've heard, you thought, ooh, shouldn't maybe not go there?

Tom Webster: 00:06:32

You know, it's funny. Like, I think any, anybody that's been to a service of any kind. The funny thing to me is how people, you know, nobody is a perfect angel.

Or, you know, maybe there are. I guess, you know, I guess I am, Danny.

But it's how people kind of dance around, you know, Bob was a complicated man, and that's always like, you know, it's Code for something like, he was actually detestable. But this is not the time or place to say that. And so it always comes out as this code that everybody can parse.

Like, you know, Jill had no problem expressing herself, as I'm sure many of you know. But there's always just that code. But you're still saying the same thing and everybody knows it.

Danny Brown: 00:07:20

It's like that passive aggressive compliment, right. Like you said, you know, that there's a story behind it and maybe you'll grab that person later, you know, over the buffet or something.

But you know, their story there. But it's.

It's weird how, like, I'm always a fan of, like, celebrating death, so I like the last two funerals I've been to, it's all been about celebrations. Not, you know, being encouraged not to be sad. You can grieve, obviously, but maybe in your own time or whatever.

And I feel like it'd be fun, for want of a better word, when you're talking about Funerals and death, etc. But it'd be fun to. To have people just roast dead people.

You know, you see these, like, roasts on TV and like, obviously, Nikki Fraser did some amazing roast. Was it Nikki Fraser?

Tom Webster: 00:08:05

Yeah. Nikki Fraser, Yeah, yeah, yeah.

Danny Brown: 00:08:06

Did some amazing roast recently. It'd be interesting to see Rosa, if you know that to your point, you. You always try to be respectful, right.

And it'd be interesting to flip that a little bit.

Tom Webster: 00:08:16

I think the posthumous roast is a fantastic idea, but I think that event would have to be invite only. You know, I think there'd be some generational issues with that. And, you know, there's a difference between friends and family.

So I think someone would have to be very selective about inviting people to that. Otherwise it could, you know, it could end in the wrong kind of tears for somebody. But I love the idea. Maybe I'll. I'll stipulate that for.

For my own funeral. Yeah. It's too bad I won't be there.

Danny Brown: 00:08:44

Oh, and that's the thing, right? You want it to be fun and silly and maybe cause a bit of. Not consternation, but just a, you know, a different environment.

But you're not going to know if that worked or not, Mario. It's like one of these things that you'll just never know, I guess.

Tom Webster: 00:08:57

Yeah. And everybody has unfinished business with the dead and the funeral may not be the place to kind of work that out.

You know, I think about when, you know, my own father died about a year and a half ago, and we didn't actually have a funeral for him. We just sort of. Okay, that's it. And there was not an unfinished business ceremony.

There certainly could have been, I think, but I think just leave that be.

Danny Brown: 00:09:23

I hear you. Well, speaking of leaving it be, and I enjoyed this one as an icebreaker, if you like, for your five questions.

Tom Webster: 00:09:30

Pretty tough icebreaker, Danny.

Danny Brown: 00:09:33

I have no control over what pops up, mate. Like, completely new for me.

Tom Webster: 00:09:37

Yeah. And now it's more about death.

Danny Brown: 00:09:40

Let's leave death and question one behind and see what we have for question two. Well, this is like a nice easy one then, to ease into that from question two. And we're recording this on a Thursday, so it's pretty timely as well.

Tom, question number two. Are you doing anything fun this weekend?

Tom Webster: 00:09:57

You know, I deeply love my wife and we have a great marriage, great relationship. Know, we've been married. We've been married 13 years this year. And for a variety of reasons, she's been gone like, 20 of the last 30 days.

You know, her. She had a trip with her two sons from a different marriage. She.

Her father had passed a little while ago, and so she had to go and take care of some business for that. So I just haven't seen her in a long time. And we're just going to have a fantastic date.

Like, we have not been out to dinner, I think, in a month, and we desperately both need it. So we're heading to, you know, a Boston hotspot, since I'm here in Boston, and we're gonna have a nice date, and I'm really looking forward to that.

Danny Brown: 00:10:44

And you'd mentioned, obviously, Tamsen's been your wife, Tamsin. She's been very busy. And you've been speaking quite a lot earlier this year, obviously, with the reports that came out.

You know, as I mentioned in the intro, there is that like a regular. Well, not so regular, maybe semi regular, where you're both kind of not passing ships.

But it's harder to organize date nights and stuff because you're both so busy.

Tom Webster: 00:11:08

Oh, for sure. I mean, you know, she speaks a lot of conferences. I speak a lot of conferences.

And there are conference seasons, you know, and so there are definitely times when we're both away from home, and those times don't overlap very well. And it can just be these, like, long stretches and complicated by the fact that we have two greyhounds and, you know, we live in downtown Boston.

There's no place to really board them conveniently. So, you know, taking care of the dogs is like, I think 90% of my life is dog management, and the other 10 is podcasting and sundry other things.

So it really does become a logistical challenge to have a date because the dogs really can't be left alone for.

Danny Brown: 00:11:51

For.

Tom Webster: 00:11:52

For too long. I mean, they're. They're anxious greyhounds, and who knows what they're going to get on, get up to when we're not here.

And, and it's not that they'll tear up our shoes and clothes and stuff, it's that they'll sit at the door and just cry. And, you know, I don't. Nobody wants that.

Danny Brown: 00:12:10

And it's going to be fun for your neighbors, I feel, having that. We have like three little dogs, and two of them can be quite loud, even though the little dogs.

Tom Webster: 00:12:17

Well, our immediate neighbor, you know, we live on the 26th floor of a high rise in downtown Boston, and we're in a corner unit, and the corner unit directly across the hall from us is the leasing office.

So that is the last thing we want are like two whining, barking dogs, or they don't really bark, but right across on the leasing office, you know, and it's. The leasing office just moved there.

And, you know, we used to, before the leasing office was here, let the dogs run in the halls just to kind of burn off some, you know, because it's hard to let greyhounds run and you can't really. They won't come back. And we were joking that with the leasing office up here, that they would.

They'd be bringing prospective tenants up to this floor, and. And all of a sudden they would see that this floor is guarded by Cerberus or, you know, some like, whirling vortex of giant dogs.

And that would be a good, A good reason not to, you know, not to live here. But anyway, it is a logistical challenge, but it's. That's what life is. So.

Danny Brown: 00:13:16

Yeah, no, I hear you. And what would be. So obviously you mentioned it's hard to organize a date. You're in Boston. I've only been in Boston once, but I loved it.

I was there many years ago, and downtown Boston especially, like, amazing place to go. What would be your ideal perfect date night? That's easy to arrange but makes for a really good memory.

So for someone coming to Boston, what would be a great recommendation for a day as well?

Tom Webster: 00:13:41

Yeah, I mean, there's, you know, people don't often talk about Boston for food, but I think, you know, a night in the, in the north end of Boston would be a lot of fun. You know, Pick any one of dozens of great Italian restaurants in the North End. It's a very Italian neighborhood. And then they're all.

They're all sort of traditional in a way that none of them serve dessert because they want you to go to the dessert place across the street or the dessert place next door, and you just sort of build a night around that. And, you know, and of course, the, you know, the. The. It's a very walkable city. There's.

There's a little brick path called the Freedom Trail that runs right outside our front door because we're right next to the old State House where the Boston Massacre happened. It's literally next door to us, but not as. Not so much massacring anymore, but, you know, it's just a very walkable city. There's so much history.

And I think for, you know, you and I both have many friends from Europe. I think it's the most European city in America.

Danny Brown: 00:14:36

ago. I think it was probably: 2012

And I had a friend. I still have a friend. He's not dead. On the subject of death. I still have a friend.

Tom Webster: 00:14:49

I had a friend. I still have him, but I had him, too.

Danny Brown: 00:14:51

Yeah, yeah, exactly. He's gonna not be my friend when he listens to this. But, yeah, I would agree with that.

It is a very, like, cosmopolitan, cultural, European vibe city, which is pretty cool to see, you know, in North America.

Tom Webster: 00:15:06

Yeah. And it's also got pockets in neighborhoods. You know, it's not a. It's not a sort of homogeneous city. It's a. It's a city where people live downtown.

I think, to me, you know, anytime you have a city where people live downtown, as opposed to, you know, commuting from suburbs and things like that, you know, I think that's a healthy city. So we love it here. I mean, you know, I actually, I did my undergraduate work at. At Tufts University, which is in a suburb of Boston.

So, you know, that was my. My formative years were here, and I've lived around the world, around the country, but I've been back here for 15 years and.

And no, no plans on leaving. I love this city. It's expensive, but, you know, it's worth it.

Danny Brown: 00:15:49

And it's home. Right. It's like you say, and it's got the. You got the wife, you got the two kids, you got the two dogs. Is it two kids? Or is it more.

You mentioned two.

Tom Webster: 00:15:56

My wife has two sons with her with her ex and they live with him in the North End. Actually they're you know, just half a mile away from us and I have a son, I have a son in college right now. So no, no kids actually at home.

Danny Brown: 00:16:10

Nice. Well, I've got like two teens at home at the moment so I'm very. Once again you're making me super jealous. You got John weep, you got no kids at home.

It's time. I have to end this episode pretty soon, mate. I'm not, not enjoying this waiting push back at me.

Tom Webster: 00:16:23

Well, you know, won't be long, won't.

Danny Brown: 00:16:24

Be long on that front on being jealous. I'm not going to be jealous of this anymore. Let's have a look at seeing what question number three brings up. Okay. And yeah, I'm curious about this.

So you travel a lot with professionally Tom, new wife travels. But what is your favorite holiday? And it can be a destination or holiday that you had, you know, prior.

Tom Webster: 00:16:49

You know, we have spent the last three years and upcoming of this summer of fourth spending lots of time in Italy and we have really, really enjoyed it.

We've gone deep on Italy and my wife has been, you know, duolingoing Italian pretty non stop throughout the whole thing and she's able to navigate things really, really well. So this, this July we're going to Torino and Milan. My wife's been to Milan, I've not been to Milan.

But you know, we've both been to Rome and Napoli and Florence and all throughout Sicily. We spent a whole week in Sicily and you know, in Palermo and Taormina and, and I've just really enjoyed it.

And you know, the first time that we went there we did a Disney adventure vacation and I highly recommend Disney vacation planning. It's, it's not full of Minis and Mickeys and goofies, is just really high end service. Right.

And we went to Sicily for a week and this is a couple years ago and it was the week in Europe that was like the hottest week on record, you know, hotter than the sun. And we spent the whole week in temperatures that were, you know, 113, 115.

I don't know how many of your centigrade that is, Danny, but it's probably hot. Yeah, it's really, really hot. Right?

Danny Brown: 00:18:11

That's 40 plus, I think.

Tom Webster: 00:18:13

Yeah. And, and in the blinding sun and with outdoor activities with two Disney Adventure tour guides and you know there were, there were 20 of us, right.

It was, it was A small group. And what kind of blew me away about it was nobody complained. Nobody, you know, everybody could have. They could have complained.

They could have, you know, moaned and kvetched and everything else the whole week, just about how dreadfully hot it was. But we all just sort of accepted it.

We drank lots of water and we had this wonderful, like, trauma bonding experience, you know, coupled with how much we loved the people and the, and the food and everything else, and it just, we just kind of fell in love with it.

Danny Brown: 00:18:58

What is it about Italy in particular? So obviously you mentioned the last four years now, or this will be the fourth year. Italy's been the agenda, the destination.

What is about Italy in particular? Is it the peak people? Is it the, the culture, like the food, etc? What. What's it for you?

Tom Webster: 00:19:12

Yeah, I think for me it's the. For me it's a lot of. It is the landscape and the architecture. You know, the food is, is incredible.

You know, we certainly, you know, especially throughout Sicily, there's, you know, people take a real pride in. No matter what the, the size, scope and budget of the restaurant is, people take a real pride in food there and it shows in everything they do.

But, you know, I just love going through, like, narrow cobblestone streets and then you all of a sudden enter a courtyard and there's this magnificent church or this magnificent fountain that, you know, and there's. There's one of those every couple of blocks. You know what I mean? It's just.

And that's true in so many cities there, and it was just really easy to navigate and the people were really, really friendly.

And I've traveled a lot throughout Europe and, and I don't have, I don't have stereotypes about, about people and cultures, but there are cities that are not as friendly, right? And, and they can be just large cities and people are busy and they don't have time to talk to strangers and, and.

But, you know, between Tamson's Halting Italian and better than Halting and my slow, loud English, everyone was really, really friendly to us. And I think, you know, it's a great, It's a great tourist destination for, I think folks in North America.

Danny Brown: 00:20:31

It's interesting you mentioned about not so much people, but cities can be unfriendly. Like, I'm from Edinburgh, but I find Glasgow a far friendlier city.

You know, not even just for Scots people, but anybody visiting Scotland, if you go, if you choose to go to, say, Edinburgh or Glasgow, you'll probably find Glasgow needs a more conversational one, open to Striking up a conversation. I think the same in Toronto. I love Toronto as a city.

Sorry, I love Toronto's people and it's a very multicultural city, but I find it's very heads down, we're super busy, we have to be someplace, you know, whereas you go somewhere like a Montreal, very friendly, very conversational, etc. It's funny how just different cities have that appeal, or not appeal, but you know what I mean.

Tom Webster: 00:21:13

Yeah, it's very true. And I think you get that experience in France, for example.

I think if you are an American in Paris, you're going to have a difficult time, but if you're an American in Toulouse or somewhere in the south, you're not.

And you know, some of it's just how, you know how fast paced the culture is and, and how much time people have to give you and, and Paris is just like New York. It's really big and full of very busy people on their way to doing something else that just don't have a lot of time for you.

And that's not the case in, in maybe some other cities in France. So I don't, you know, I don't typically tend to stereotype the French because I've just had so many different experiences there.

I do have a funny Glasgow story. This was back in the, gosh, in the late 90s.

I used to do a lot of consulting work in radio throughout the UK and one of the things that I often consulted on were OFCOM applications. OFCOM is this entity that you basically that regulates who gets radio signals and who can start new stations and things like that.

And often in a city an application opportunity would come up that, the, that the city, that Ofcom would allow a new signal in that city. And so you'd have to do applications and you'd have to show research and do and do your work.

And so I did a lot of that research and consulting and I worked on an application in Glasgow and I did, I did some music testing there and I was there with a colleague of mine, his name was Hal.

And you know, Hal was up there playing music off of a, off of, you know, he had a, he had a laptop because we had this sort of electronic testing thing like dials. People had that they were responding to these various snippets of songs, you know, how much they liked them or didn't like them.

It was in my late 20s, I guess, and you know, we'd played about 50 of these song clips and all of a sudden this guy at the very back of the room like full beard, thick cable knit fisherman sweater, raises his hands and Hal goes, yeah, sir, do you have a question? And he stands up and he goes, Hal, have you no got better music in your computer, man?

I'll just never forget that because that kind of, you know, threw off the rest of the night a little bit, but just killed me, Hal.

Danny Brown: 00:23:33

And I love the fact he's got his big raggling on, you know, he's probably coming from doing some fisher fishing, you know, catching some of the fish.

Tom Webster: 00:23:39

Undoubtedly undoubted. Yeah. Just straight off the boat.

Danny Brown: 00:23:43

It's funny you mentioned Ofcom there as well because I feel if I remember, it's been a while since I've not been in the UK for 20 years and so I forget terms, etc. But isn't Ofcom just simply the Office of Communications? That's what it stands for.

Tom Webster: 00:23:57

Yeah, that's right, yeah.

Danny Brown: 00:23:59

sort of Harry Potter kind of: 1984

Tom Webster: 00:24:10

It's a bizarre system.

You have to, basically, when you put in, this may be way off topic, but when you apply for a new station through Ofcom, you have to show that it's not going to materially compete or materially damage other commercial radio stations in that market. It's fine if it competes with the BBC, but it's not, you know, like here in America, the cities are very over radio, there are too many signals.

You have, you know, three or four country stations in a market. This with we have Spotify, we don't really need three or four country stations, we need one great one.

But you know, in with Ofcom, if there's an existing station in your format, you can't just start a signal and do that and try and do it better. You have to show that, oh, we wouldn't harm them at all. And it's a very complicated system.

But you know, it was a, I've, I've won a few and I've lost a few.

Danny Brown: 00:25:01

That's interesting. I never knew that about Webcom.

So they're encouraging, like, I guess encouraging growth in, you know, smaller radio stations because you, you can't open up something that's already there. So it kind of protects a little guy from that side, I feel.

Tom Webster: 00:25:14

Yeah, and I, you know, honestly I, I agree with all that.

I mean, I, you know, we have none of those protections here in the United States and as a result we have a very unhealthy commercial broadcast radio, you know, that's in constant decline, that has too many ads, too much repetition and replication in markets and it could do with some regulation because I, you know. But that's another show.

Danny Brown: 00:25:38

Well, yeah, it's funny, I wear. I have another podcast that I co host with my colleague from Captivate where I work, called in and Around Podcast.

And then last night I recorded an episode with James, our friend James Gridland from POD News. And he's obviously a big, huge radio. He's got the radio background as well.

I feel that you two together could have an amazing conversation about the ends outs, the do's, the don'ts of radio and where it could go.

Tom Webster: 00:26:01

Yeah, I just think, you know, a lot of the attitudes about radio in America are, are influenced by American radio. And there's a couple of really big differences in American radio. American radio is largely deregulated compared to other markets.

Most markets, especially in Europe, are very protected. And the other thing that America does not have, which, you know, any European country does, is a state broadcaster.

America doesn't have a state broadcaster and a state broadcaster. It's not a sinister thing.

It is, it's a wonderful thing with, it's a, you know, high budget, lots of investment, people take pride in it, you know, and that's, that's true across, you know, pretty much all of Europe and there aren't so many commercial radio stations, you know, they can all sort of coexist in a market and, and do very well and, and you know, that the European radio market is much, much healthier.

The American radio market unfortunately has shot itself in the foot in a number of ways and you know, they're kind of burning the furniture to keep warm.

Danny Brown: 00:26:59

So it's a shame to see. I know, like I mentioned, James, I'm very much in radio background, but it's a shame to see.

I know a lot of the local stations here are struggling because of, you know, streaming services, you know, Spotify, Amazon Music, etc. And I grew up as a, listening to radio. Like my granddad would have it on and listen to it. We'd listen to the sports results coming through.

And you don't get that now, you know, you just check your phone and say, okay, yeah, great team one. And that's a shame to see that.

Tom Webster: 00:27:23

Yeah, I agree. I mean, you know, I grew up with great radio as a, as a companion.

And you know, one of the things that the, that the radio business in America did in response to things like, you know, Pandora and, and then Spotify and some of the other services was they, they tried to out Pandora, Pandora and they, you know, they shut their personalities up and you know, as a result of that they just became the same thing, except with 20 ads. And that's simply non competitive, especially for Internet radio.

Danny Brown: 00:27:54

Yeah, I hear you. So there you go, listeners. If you want to have Tom, you know, really go on a deep dive, ask him about radio.

And I feel we could speak about this for hours and hours, but we don't have hours and hours, unfortunately, Tom, so we don't. Let's have a look at question number four. Okay, here we go.

This is like a bit more of a serious one maybe question number four, Tom, what is your biggest regret?

Tom Webster: 00:29:31

Wow, my biggest regret? I, oh man, I try not to have too many of those in life, I really don't.

But I will say something that I think probably a lot of people share that have had my experiences, both, you know, men and women. I'm divorced and you know, I have a, Tamson is my, my second wife, my first wife is a, a brilliant molecular biologist. She's a university professor.

And you know, I think anytime you have a marriage end, you have to have regrets, right, because you entered into it not thinking it was going to end and you ended it knowing it had to end. And in between that was all series of cascading missteps by one or both of you, likely both of you.

And I think I would regret, I don't, I don't know that I really want to get too specific about it, but I do think second marriages are wonderful. I think you're much clearer about what it is that you want and don't want and you spend the time getting to know that person a little bit more.

And you know, I, I don't believe I've made any of those mistakes with Tamson. So, you know, knock on, knock on Felton Wood here. I hope I, I don't have a second regret.

Danny Brown: 00:30:59

I, I hear you. I, I, I think that's like you say, it's something that, you know, anybody that's been through it as well can understand.

I know my wife's mum, she doesn't listen to the show, so she's okay, I'm okay.

But I know it's Mum, she's been married three times, she's on her third marriage and there's a running joke in the family about, you know, is this one going to last, is it not going to last, etc.

But she does say that each time she takes something away from what, what she learned from marriage one or marriage two, and what kind of person wasn't right, the, the dynamic, etc. And this has been her longest marriage, longest lasting.

So I feel like, you see there, there's definitely regrets of anything that ends like that, but the lessons can help you, you know, to the next stage of what that looks like.

Tom Webster: 00:31:47

Yeah.

And I, you know, I don't believe I would be to the extent that I am a good husband, as good a husband I am to Tamson without the things that I, I really learned from that first marriage. So, you know, I wish, I hope it doesn't take multiple for everybody, but sometimes it does.

Danny Brown: 00:32:04

Yeah. And you'd mentioned that obviously there's kids from the first marriages etc, as well.

I know a lot of times, maybe more with people that date as opposed to being married, but maybe married as well. A lot of times there's recommendations you should stay together for the kids. Do you think that's in general bad advice again?

You don't have to be too specific, mate, but it's terrible.

Tom Webster: 00:32:26

It is absolutely terrible advice. Yeah. I was such a better. So my son, my son is now 20. He's a sophomore at Colorado Boulder.

And you know, when I, when, when we got divorced, he was fairly young. I think he was maybe five, something like that. And, and I was a much better father to him after that.

And I think what he ended up getting as a result of that was his mother's undivided attention when, when he was with her and my undivided attention when he was with me. And you know, was it, was it disruptive? I'm sure it was disruptive, but I don't know. He's on a full scholarship with straight A's in college.

He did okay. I'm incredibly proud of him. And you know, would that have happened had we stayed together?

I, I don't doubt that it would, but it would have been a different and, and potentially more difficult experience. So I think staying together for the kids is really outdated advice.

I think providing as the fewest disruptions and the most support for your kids as possible, whatever that means. That's the advice.

Danny Brown: 00:33:37

No, like I said, I've got two teens and if my wife and I ever did divorce, I'd like to think we could still be friends. And we do amicably and we understand that we're doing it because we don't want the kids to be disrupted. Right.

We don't want to see us fall out of love with each other, hate each other, than get really bad and what all that could bring.

Tom Webster: 00:33:56

Yeah, I mean, you hope that's true. You know, I think it took my ex wife and I many years to kind of get to that level of detente, I think.

But in no case did we ever, you know, litigate this in front of our son. So I think ultimately it was good that we divorced.

Danny Brown: 00:34:13

And as you mentioned, it's, and this Sounds flippant, I 100% apologize, but it all worked out for the best because now, you know, you're happy, I'm assuming. Hopefully your ex wife is happy and obviously your son is doing really, really well in his life as well.

Tom Webster: 00:34:27

Yeah. No regrets about any of that.

Danny Brown: 00:34:29

That's always good to hear. Well, Tom, we've almost made it through to the end, so without further ado, question number five. Interesting.

So that kind of ties in with the one we've just had, I guess. But let's have a look anyway. Question number five. Would you rather be rich and never find true love or be poor and find true love?

Tom Webster: 00:34:52

I would say I would rather be poor and find true love, but I mean, I did not grow up in wealth and you know, I, I, I can make it work, you know what I mean? But I do know how important it is for me to have a partner. And especially because, you know, I don't know about you, but I'm a real introvert.

I'm an incredibly introverted person. Right. You know, you put me in a room at a party or something like that and I will not talk to anybody if, unless they come and talk to me first.

And that's one of the reasons why I, I worked to get really good at public speaking. Because when I go to an event and I give a keynote, people will come up to me and that's helpful to me.

So, but you know, having that sort of one great partner in your life, a lot of pressure on them. But I would rather have that than all the gold in the world.

Danny Brown: 00:35:42

It's, it's like that the old saying, right? If you want to be truly rich, be happy. You know, you can have all the gold in the world, all the riches, like everything.

But sometimes, I mean, you look at some celebrities and they look as if life is amazing.

They've got millions in the bank, they've got yachts, private jets, you know, celebrity hanging off like, you know, beautiful looking dates, men and women, when they go to events, etc.

But then you see them after and they've got, they just look unhappy and you know, sometimes get into bad places through whatever reasons it's yeah, I feel like the real happiness comes deep inside like you say, where it makes you be a better person and be a really content, happy, confident person maybe.

Tom Webster: 00:36:26

Well here's my stipulation though. I would rather be poor and find my true love. One of my criteria for my true love is that she be incredibly wealthy.

Danny Brown: 00:36:37

And you know, if anything touch, touch wood, touch my felt kind of gaming mat, desk wood hanging. This never happens.

But if anything ever did happen between you and, and Tamsin, maybe there's a rich Italian widow waiting in Sicily or you know, somewhere like that that could, you know, on, on one of the destinations on one of the vacations way in the future.

Tom Webster: 00:37:00

I think by that time Danny, I would be more inclined to just pull a long con on, on that, on that widow and just spend just enough time with her to get sort of, you know, get her to trust me, get access to her checking account and then, and then I'm gone. It would just be a long con if that ever happened. So don't, don't be surprised.

Danny Brown: 00:37:23

Well I was going to say, I mean that's very specific there about how you would do it. It sounds like you've been thinking about this in the background, mate.

Tom Webster: 00:37:29

I've taken notes over the years so. Look, you just have to be prepared for anything, Danny.

And you know, you never know what life is going to throw you and if circumstances ever change in my life I have to be prepared for a life on the run.

Danny Brown: 00:37:43

It's like I watch this TV show in the UK I watch on YouTube now it's like broadcast in the UK and it's got would I lie to you?

guests was saying he'd buried: 1000

I guess you would need a good backing behind you for life on the run.

Tom Webster: 00:38:15

Yeah, exactly. I think, you know, I should, I should be burying things in cities all across the world. Danny, I think that's probably a good idea.

You know, just have a go bag in every city for, you know, when it happens.

Danny Brown: 00:38:28

Exactly.

Well, speaking of the unexpected and speaking of planning things out, we've got to the end of the five unexpected random questions and it's as Is the, the only fair thing to do now I've had you in the hot seat for the last 40 minutes now, so it's time for me to pass the baton over to you, Tom, and throw open to your random question.

Tom Webster: 00:38:47

Yes, well, my question is not random, it's, it's thought about it. And, and that is. You know, Danny, I've known you for a number of years.

You know, I think we first met at maybe like a blog world or something like that in a, in a very different life. Right. And what's been the biggest change in your life since then and what prompted it?

Danny Brown: 00:39:10

ng to Canada, I guess back in: 2006

I wasn't a media or anything. I was like a typical corporate marketer working for British Telecom. So it was like a very, very different person then, I guess.

But yeah, I got to meet my wife online on the Dashboard Confessional official website forum. Music again. So music is my background. I feel like yours as well, mate. Music has so many histories and the question was, do I move to Canada?

Does she move to the uk? And I felt like she had a much more strong family base than I did.

I don't really keep in touch with my family with a big fallen out, which is another story for another time, but a big falling out. So I don't really keep in touch with them. So it made that decision easy.

But then I had to sort of reinvent myself because I was going through visas and work permits and stuff like that. Did a lot of crappy freelance gigs originally.

And Jacqueline, my wife was amazing and her mum was amazing at supporting us as well while we got started.

So that would probably be the biggest change is being a super corporate, super business, career minded guy to being now where I don't really give a crap about, you know, financial, you know, success and blah, blah.

Be nice to have money, but I don't give a crap about that and living in Canada and having two kids and raising kids, you know, and then move into like a tiny little village where we live now as opposed to just outside Toronto where we used to live. So probably a big change from super corporate super business to like life is life.

And maybe that's a sign of getting older as well, changing priorities, right?

Tom Webster: 00:40:58

I think so. I mean, I think that's just a sign of, you know, being increasingly comfortable in your own skin as much as anything else.

Danny Brown: 00:41:06

Yeah, it's funny you mentioned you're an introvert as well. A lot of podcasters, a lot of creators are introverts. I'm very introverted. I hate networking. I ha big events like podcast movement.

I'd rather be in the corner with someone I feel really trusted and safe with and just chatting with them.

Tom Webster: 00:41:20

That's totally me.

And actually that's one reason why my partner at sounds Profitable, Brian Barletta, and I are such a good fit, because Brian really understands me, like thoroughly understands me.

And he knows that, you know, after I give, he's energized by people, you know, and if he wants, you know, if I want to meet somebody, he will introduce us. Like, he will just dive right in.

And he also understands that when I'm done giving a keynote or something, that regardless of what it looked like on stage, I'm exhausted. And he understands that this is not the time to ask me to do anything.

This is the time to like wheel me into carbonite storage until I'm ready to come out. So that partnership has worked really well.

Danny Brown: 00:42:07

If I'm at an event where you are, I shall hunt you down. That sounds awful.

I shall look out for you and keep me, maybe try to keep you occupied for 5, 10 minutes at least where you don't have to worry about anybody else.

Tom Webster: 00:42:17

That would be lovely.

Danny Brown: 00:42:17

And I'm being selfish there because that would be great for me too. Just to hang out with one person.

Tom Webster: 00:42:21

That would be lovely.

Danny Brown: 00:42:23

We shall look forward to it. So again, Tom, I really enjoyed getting to know a little bit more about you away from the professional side that we generally hear from you.

For people that want to know more about sounds profitable, about what you do from a speaking point of view, about your musical tastes, etc. Where's the best place to either follow you online or connect with you, et cetera?

Tom Webster: 00:42:42

Yeah, I mean, soundsprofitable.com has a huge treasure trove of resources about podcasting and our LinkedIn page does as well. I can be found on Bluesky, and I think that's Tom Webster Media, I think is my account, I believe, at bluesky.

And that is not typically a place where I talk about marketing and business and things like that. That's generally where I share funny photos or, you know, or music related things.

So I try not to cross the streams on social media all that much because that gets, that gets really tiresome.

Danny Brown: 00:43:15

I hear you and I'll be sure and obviously Like I say, Tom does make me jealous because he drops stuff on Bluesky about gigs he's going to and people I'd love to see live. So yeah, if you want to upset me even further, follow Tom and just like share his stuff with me anytime. The music stuff, fantastic.

But I will be I will be sure to leave these links in the Show Notes as always. So if you're listening on your favorite podcast app or listen online on the website, check out the show notes for the episode.

All the links will be there to take you through to Tom. So again, Tom, thank you so much for appearing on today's five Random Questions.

Tom Webster: 00:43:44

Danny, it's been a pleasure. Thanks for having me.

Danny Brown: 00:43:47

Thanks for listening to five Random Questions. If you enjoyed this week's episode, I'd love for you to leave a review on the app you're currently listening on.

And if you know someone else that would enjoy the show, be sure to send them the this way. It's very much appreciated. Until the next time, keep asking those questions.