[00:00:00.09] JESSE WEDLER: Got this idea of buying a piece of property and putting a bunch of cabins or bungalows on it and having some sort of mix of like a family compound but where you could also rent it out, have big groups of friends. And it probably wouldn't be that much of a career, but it'd be a really fun hobby.
[00:00:15.87] [MUSIC PLAYING]
[00:00:18.66] REID HOLZWORTH: This is the Insurance Technology Podcast where we bring interesting people from across the insurance ecosystem to discuss and debate technology's impact on the industry. Join us each episode for insights and best practices from industry stewards and tomorrow's innovators.
[00:00:36.46] SPEAKER 1: Today, in the Hot Seat for the Insurance Technology Podcast, I have Jesse Wedler with CapitalG. Welcome to the Hot Seat.
[00:00:44.71] JESSE WEDLER: Thank you. Excited to be here.
[00:00:46.42] SPEAKER 1: So before we get into, like, the big interview with Reid, I just wanted to ask you a couple of personal questions so that our listeners can get to know you better.
[00:00:55.68] JESSE WEDLER: It's all good.
[00:00:57.00] SPEAKER 1: First one, favorite movie?
[00:00:59.97] JESSE WEDLER: So I don't think I have a favorite movie now, but the favorite movie I had for the longest time was Speed. Remember that Keanu Reeves movie back in '94? It's a pretty terrible movie, but when I was, you know-- when I was, like, early teen years I was like, this is incredible. I probably watched it 100 times.
[00:01:15.56] SPEAKER 1: Yeah, yeah, that was probably one of my favorites. And I also think too, like, Keanu Reeves likes to do, like, multiples. He did multiple Speeds. Now he's got multiple John Wicks.
[00:01:25.22] JESSE WEDLER: Yeah, they hijack the bus. That was a good one.
[00:01:28.67] SPEAKER 1: Favorite music genre?
[00:01:31.46] JESSE WEDLER: I'm kind of a classic rock and reggae type of guy. You know, I listen to some Van Morrison, listen some Slightly Stupid, some old reggae.
[00:01:40.49] SPEAKER 1: Nice. So on the music theme, last concert you attended?
[00:01:46.10] JESSE WEDLER: I saw Rebelution up in Bend, Oregon, at the amphitheater out there. It's a great, great little venue outdoors. It was a good show.
[00:01:56.72] SPEAKER 1: I love outdoor theaters.
[00:01:59.84] JESSE WEDLER: This one's right on the river, on the Deschutes River. So people watch it from their canoes and kayaks sometimes.
[00:02:05.03] SPEAKER 1: Oh, that's cool.
[00:02:05.66] JESSE WEDLER: And it's just got a good local feel, small, beautiful view. It's a fun spot.
[00:02:12.97] SPEAKER 1: So we're changing it up a little bit. And I always say that we add these questions in because of Reid being a car guy. So first car you drove?
[00:02:22.66] JESSE WEDLER: Ford Aerostar. Parents' hand-me-down minivan with fold-down back seats. It was the camper edition, so we did some good camping trips in that. It was fun.
[00:02:32.50] SPEAKER 1: Love it. My husband actually got his mom's minivan and it's amazing. All of a sudden, you're like, I don't want a minivan. But then you realize how many people can get in the minivan, and you're driving everybody everywhere.
[00:02:43.67] JESSE WEDLER: High utility. Yeah, it's kind of a rite of passage, yeah.
[00:02:47.62] SPEAKER 1: So current car?
[00:02:49.74] JESSE WEDLER: Ford F-150.
[00:02:51.87] REID HOLZWORTH: I wouldn't expect that, Jesse. I feel like you'd be like a Tesla guy or something.
[00:02:55.86] JESSE WEDLER: Yeah, you know, my daily driver is the F-150.
[00:02:59.64] REID HOLZWORTH: Love the F-150. A newer one?
[00:03:02.04] JESSE WEDLER: Newer one. No, pretty like a few years old. Lariat, gas, not electric. But you know, it takes the family around, fun to drive, tows the boat. It's all around easy. Parking it is kind of a pain around town, but that's about it.
[00:03:18.36] SPEAKER 1: All right, two more. If money was not an object, what would you be doing for a career right now?
[00:03:26.14] JESSE WEDLER: Well, I don't know if I'd be doing a career per se, but I would be doing a mix of probably cruising a sailboat around the Pacific and probably running some sort of lodge up in Oregon. Got this idea of buying a piece of property and putting a bunch of cabins or bungalows on it and having some sort of mix of, like, a family compound where you could also rent it out, have big groups of friends. And probably wouldn't be that much of a career, but it'd be a really fun hobby.
[00:03:52.32] SPEAKER 1: Yeah, no, that sounds awesome. All right, last one, why did you agree to be on the podcast?
[00:03:59.50] JESSE WEDLER: Because Reid's the man.
[00:04:02.64] SPEAKER 1: See, a lot of people say that. [CHUCKLES]
[00:04:04.59] JESSE WEDLER: OK--
[00:04:05.01] SPEAKER 1: That's the answer.
[00:04:05.46] JESSE WEDLER: --I'm not the first? Yeah, yeah, no, I was stoked to get invited and excited for this.
[00:04:13.02] SPEAKER 1: All right, well, thank you so much for sitting in the hot seat.
[00:04:15.66] JESSE WEDLER: Thank you.
[00:00:15.87] [MUSIC PLAYING]
[00:00:18.66] REID HOLZWORTH: This is the Insurance Technology Podcast where we bring interesting people from across the insurance ecosystem to discuss and debate technology's impact on the industry. Join us each episode for insights and best practices from industry stewards and tomorrow's innovators.
[00:00:36.46] SPEAKER 1: Today, in the Hot Seat for the Insurance Technology Podcast, I have Jesse Wedler with CapitalG. Welcome to the Hot Seat.
[00:00:44.71] JESSE WEDLER: Thank you. Excited to be here.
[00:00:46.42] SPEAKER 1: So before we get into, like, the big interview with Reid, I just wanted to ask you a couple of personal questions so that our listeners can get to know you better.
[00:00:55.68] JESSE WEDLER: It's all good.
[00:00:57.00] SPEAKER 1: First one, favorite movie?
[00:00:59.97] JESSE WEDLER: So I don't think I have a favorite movie now, but the favorite movie I had for the longest time was Speed. Remember that Keanu Reeves movie back in '94? It's a pretty terrible movie, but when I was, you know-- when I was, like, early teen years I was like, this is incredible. I probably watched it 100 times.
[00:01:15.56] SPEAKER 1: Yeah, yeah, that was probably one of my favorites. And I also think too, like, Keanu Reeves likes to do, like, multiples. He did multiple Speeds. Now he's got multiple John Wicks.
[00:01:25.22] JESSE WEDLER: Yeah, they hijack the bus. That was a good one.
[00:01:28.67] SPEAKER 1: Favorite music genre?
[00:01:31.46] JESSE WEDLER: I'm kind of a classic rock and reggae type of guy. You know, I listen to some Van Morrison, listen some Slightly Stupid, some old reggae.
[00:01:40.49] SPEAKER 1: Nice. So on the music theme, last concert you attended?
[00:01:46.10] JESSE WEDLER: I saw Rebelution up in Bend, Oregon, at the amphitheater out there. It's a great, great little venue outdoors. It was a good show.
[00:01:56.72] SPEAKER 1: I love outdoor theaters.
[00:01:59.84] JESSE WEDLER: This one's right on the river, on the Deschutes River. So people watch it from their canoes and kayaks sometimes.
[00:02:05.03] SPEAKER 1: Oh, that's cool.
[00:02:05.66] JESSE WEDLER: And it's just got a good local feel, small, beautiful view. It's a fun spot.
[00:02:12.97] SPEAKER 1: So we're changing it up a little bit. And I always say that we add these questions in because of Reid being a car guy. So first car you drove?
[00:02:22.66] JESSE WEDLER: Ford Aerostar. Parents' hand-me-down minivan with fold-down back seats. It was the camper edition, so we did some good camping trips in that. It was fun.
[00:02:32.50] SPEAKER 1: Love it. My husband actually got his mom's minivan and it's amazing. All of a sudden, you're like, I don't want a minivan. But then you realize how many people can get in the minivan, and you're driving everybody everywhere.
[00:02:43.67] JESSE WEDLER: High utility. Yeah, it's kind of a rite of passage, yeah.
[00:02:47.62] SPEAKER 1: So current car?
[00:02:49.74] JESSE WEDLER: Ford F-150.
[00:02:51.87] REID HOLZWORTH: I wouldn't expect that, Jesse. I feel like you'd be like a Tesla guy or something.
[00:02:55.86] JESSE WEDLER: Yeah, you know, my daily driver is the F-150.
[00:02:59.64] REID HOLZWORTH: Love the F-150. A newer one?
[00:03:02.04] JESSE WEDLER: Newer one. No, pretty like a few years old. Lariat, gas, not electric. But you know, it takes the family around, fun to drive, tows the boat. It's all around easy. Parking it is kind of a pain around town, but that's about it.
[00:03:18.36] SPEAKER 1: All right, two more. If money was not an object, what would you be doing for a career right now?
[00:03:26.14] JESSE WEDLER: Well, I don't know if I'd be doing a career per se, but I would be doing a mix of probably cruising a sailboat around the Pacific and probably running some sort of lodge up in Oregon. Got this idea of buying a piece of property and putting a bunch of cabins or bungalows on it and having some sort of mix of, like, a family compound where you could also rent it out, have big groups of friends. And probably wouldn't be that much of a career, but it'd be a really fun hobby.
[00:03:52.32] SPEAKER 1: Yeah, no, that sounds awesome. All right, last one, why did you agree to be on the podcast?
[00:03:59.50] JESSE WEDLER: Because Reid's the man.
[00:04:02.64] SPEAKER 1: See, a lot of people say that. [CHUCKLES]
[00:04:04.59] JESSE WEDLER: OK--
[00:04:05.01] SPEAKER 1: That's the answer.
[00:04:05.46] JESSE WEDLER: --I'm not the first? Yeah, yeah, no, I was stoked to get invited and excited for this.
[00:04:13.02] SPEAKER 1: All right, well, thank you so much for sitting in the hot seat.
[00:04:15.66] JESSE WEDLER: Thank you.