Achieving anything great involves taking a gamble; and failure is always a possibility. Step into the lives of people who take on unknown odds every day to offer others a chance to achieve their dreams—with a firm safety net beneath them. We’re talking about the risk-assessors—and risk-takers—in the world of insurance. Gaby, Alain, and Jenna are all interested in the varied paths of insurance, and set out to talk to cyber risk managers, catastrophe modeling pioneers, entertainment brokers, and more who’ve made risk their business. As they travel from coast to coast, the roadtrippers uncover endless possibilities in the field they never imagined—and see how a career predicated on uncertainty can actually bring peace of mind to people the world over.

Risk & Reward

INSIGHTS FROM THE FILM

Travelers

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It sounds like a contradiction: one of the most steady careers out there is also one that involves the most risk—and proves you can’t gain without taking a chance.

My biggest fear is kind of not having any direction after college. And then saying to my parents, I don't have a job. &gt;&gt; This summer, I am taking this road trip all over the country in a huge green RV with two other students. I'm gonna be interviewing leaders in the insurance industry. Those people are hopefully gonna provide me with some kind of insight into how they got where they are, what advice they would give me for the future. &gt;&gt; Everything works because of risk aversion. It is fundamental to human behavior, how we think about risks. &gt;&gt; I think that risk is super scary, so I think doing this road trip will be really good for me. Ready? Aah! &gt;&gt; So I calculated the risk of dying in a crash over the course of the entire trip is about 25%. But that's what insurance is for, right? &gt;&gt; I haven't been a very risky person in my life so far. &gt;&gt; Fear of failure has stopped me from taking different chances on things. &gt;&gt; Anyone who ever did anything started by rolling a dice, taking a risk, right? &gt;&gt; Without risk, nothing would be rewarding. [MUSIC] 

Insurance Roadtrip Trailer

confront risk face-to-face around unpredictable odds? of insurance, risk isn't just itself. Roadtrip Nation  country to uncover  improbability your profession. the risks behind to help people Risk & Reward. >> Surprise. >> What's up guy's? To the RV! in Boston. developing yourself of people, and all three of us backgrounds. really happy to see them as if haven't seen for ages. us all to be together. person or Bachelorette person? bachelorette. >> When I was talking about like, so it's basically like The Bachelor? you're choosing out of- they're on cameras and that's about it. >> Cameras. risk of dying in a crash over is a total of 0.00346%. but we're driving a big RV. accidents. our new risk of dying here that was just an estimation. right? I'm in. >> Yeah, >> Nice, big fridge. >> That's a freezer. cream. got it's got beds, CD player, it's  my dream house. >> There's no- >> I'm really excited. unpack my bag and know that it's unpacked for >> Behold. cooker! outlet here? the best thing I have ever seen. this. than I needed, the other two  packed lighter than I did and [NOISE]. >> [LAUGH] going to be a senior at I'm from Fraser, Michigan. you know people but don't know everybody. As a kid I was super outgoing, active. dancing even though I'm awful. to entertain somebody. honors classes, a lot of AP classes. was really good, academically. being away from my family. literally calling her 20 times a day. doing general business, I was  like play it safe. Olivet, in the insurance department. change my major to insurance. me that insurance is really  about helping people people have peace of mind. do you need insurance. what? insurance and I'm like a little  nerd now. [LAUGH] management. But I don't know if that's 100% what I want to do. failure has stopped me from chances on things. I wouldn't have failure. think this road trip is a big risk. driving this huge vehicle. connections and hear people's stories. opening myself up to even more parts of insurance that I yet. a lot about myself. to learn about myself. looking forward to. duck, because like on the  surface I'm, like, chill. mad. >> [LAUGH] be? >> I'd be a Squirrel. University of Connecticut where I currently study calculate how much loss you're gonna have. my parents gave me an option a prestigious college in Japan. keep going through high school. me to spend my life in Japan. respected my decision to stay here. choose which country I want to live in. they made the right decision of keeping me here. have an ambition or a drive. was right at the moment. knew my strengths and  weaknesses. a fit for actuarial science, really thrive in this major. focus. able to present my value or workplace and biggest fear. coming back home to this house And I don't have a job. direction after college. what's important for to become independent. don't have to worry about me. important to find that path for  yourself. that you really want to do. essential to find people that  went through this road trip is perfect for that. [LAUGH] what valuable lessons I learn. noise when I put my foot on the  break? parking break. >> Is that this? we're going to be interviewing people who have found love within the insurance industry. they got to where they are, and insurance. >> So today we are going to Ries >> How are we doing? through all of our notes on like what to ask and everything just because all three of us are super talkative. interview and I'm really excited for it. insurance carrier. to prevent a property loss. heading up a team to help our as well. issuing a policy, it's so about premium. when you can shoot things, and shake things. sign me up. doing the wet lab. Sprinklers are good, but not enough. how to evaluate that water supply, gonna be doing today. anything like this before? hard. culture where my parents were  advising me, career. a lawyer, or an engineer. wanting to be an engineer. an insurance industry, but of faith. manager of cyber risk insurance products. sure I'm sane, it's not crazy. Grace? to see if I will like it. really enjoy it. us- for the next couple of weeks? >> Think about right? >> Yeah, >> Sign yourself up for uncomfortable to you. just try to be part of it. you can bring to the table. industry, stuff that I could work in. carry on building on that so I don't have another mid life crisis people either go down the  route. decision, that I picked both. scared to rule out an option. parents had always said to them, you'll be a great lawyer, or that kind of thing. wanted to do. made for them, and I was kind of envious of that. would tell me what to do. we can't make this decision for you. so I ended up doing math and science. really hard times in their lives when I was younger. he would start a job he would think it was great, realized actually wasn't for him. that he really loved. because he was never happy in what he was doing. about what I wanted to do with  the rest of my life, about. something I was happy doing. down the line that the job wasn't for me, don't really know what to do  with that freedom. a car insurance company. for when I graduated. would do, but interesting because it's looking at statistics, and something is statistically relevant. the mathematics side of me. in insurance as a whole. insurance would be that exciting. I gonna get up one day and and talk about insurance. things I can be excited job to look forward to. think about what if I am worried that the next 40 years, and end up  being very miserable. to somebody who at my age felt, they were doing with their life. people know what they want and they chase it. chasing. somebody to say, you didn't intentionally go out and find. found that right thing for you. reassurance more than anything. meet you. >> Hi, nice to meet you. introduction of company does, that kind of  thing? determine what potential types of natural catastrophes. the models, and I guess the  industry, inventing so many years ago, years ago. >> [LAUGH] data, that could simulate potential  future earthquakes. couple of weeks ago that  basically said in the FTSE the name John than there are women. >> [LAUGH] CEO who is kind of self made and I was like, my God, you've done so much. I really wanna come and interview you. doing at our age, and how did you doing now? >> Well, I have to tell you that at your impressed at all of you are pretty do >> I remember in graduate school, and I took it right away. insurance company, which unlike  you in fact, I would have said no, because it's so boring. okay, I'm just gonna go for it,  and lo and to do something about hurricane risk. modeling I started in 1987. up devoting my whole life to it. biggest thing is I've kind of  fallen into the job I have. while I was at university, and  it just so company offered me a job. am I just taking this job because it's to me, or do I actually really love it? know? >> Well, you won't know, so it's not gonna be the right decision. you will not stay there forever. hopefully, you'll learn more  about what you like and gonna be my whole career, passion. I felt that I had to do. you can influence. something, you're gonna make people believe that too. was to Lloyd's of London back in 1987, what we're doing now is impossible. are about 150 of them in the room, come in, and seven months pregnant. it was some kind of a joke. paying attention the first ten minutes. punch line? >> How did you deal with that like, up? >> Well, I was so focused on what I was doing. disheartened. how can I still do this? be focused on what you're doing. through and company and tackling something that it's very scary step to take, right? any doubts over the years on >> Sure. and there are a lot of doubts. do something, you wanna try it, not happy in your, what you thought was your chosen when you get up every morning, on whatever you're working on. this, and you think you're good at this other thing. regret having done things, not having done things. you are going to be happy. looking forward to the next 8  hours or it may be. you talk to anyone who knows me, they think, you know what, I never worked a day in enjoyed everyday of my career. fireworks for the 4th of July, me because it's my first 4th of July. Americans get over it. there were some like, performing arts students next to us and like, I should sing too, >> And then, we were just laughing and what are the odds you'd do that? joined in with us. was kind of just stood like, I don't know the words. >> [APPLAUSE] >> [APPLAUSE] >> I'm gonna be in different person by major is to avoid risk. Jenna and Gabby gotten other's differences but I like, >> Today, it's been a lot of fun. are gonna go really quickly and >> Wow. >> [LAUGH] 

The road trip begins! First up in Boston: Grace Ries, cyber risk expert, and Karen Clark, catastrophe modeling pioneer.

All Bets Are Off

York. trip. the road trip has gone so fast. are going to go really quickly. going. people in there. see all the touristy stuff. walk around with people that out of our comfort zone. my wheels start turning more and with my life? next possible thing could  happen or there's things that I am not going to be prepared for and going to have to get used to. kind of guide me in so I can turn to them. shore to interview Laura Woop. the Risk Management for Tiffany and Co. about her because I'm leaning  towards risk that's 100% what I want to do. >> I'm Jenna. How are you? director of risk managment Tiffany and Company. responsible for insuring the assets of the company, our jewelry, our property, our building. interesting risks happening  within Tiffany every day. as a more risk adverse person? adverse person, I'm a risk aware person. bit about your childhood? my stepfather was a police officer. family. college push so it was kind of how I was going to navigate my way through college. accounting, and recruiting with Tiffany & Co. what Tiffany company was, I  didn't grow up in jewelry or any of that kind of  stuff. asking if I wanted to interview with Tiffany and position in the internal audit department. there. about five years and it just so opening and went into risk management. management I had no insurance experience. I owned a homeowners policy and experience. very strong resources through our insurance brokers. on, and I would ask all the stupid questions. resource to train me and to know about insurance. experience along the way. understanding that you're talking about insurance. open to folks from different  backgrounds. going to go into insurance. majoring in it. read my book, I'm trying to catch up on you know lost program were in there for three  or four years. me if you need. >> Okay. I have realized in my career is  if you have the something, we can teach anybody to do anything. you've taken that perhaps  haven't paid off or that maybe you regret. risk was moving into risk  management, of totally moving away from this thing I went to school for. that right on the backburner. the fact that I've area enabled me to be asked to do these other things. running our credit card program, it's different kind of risk. all of our online orders to make sure that it's order online, and not someone like Alain, >> So blossomed into a very nice  career for me. insurance because yes, it is the insurance industry, an insurance policy day in and day out. opportunities, it's not going  to remain static. will change. media, it's changed for lots of reasons, and I would say just be open to exploring it and questions because when I went into this it was the dumb ones too or what seems like it. questions. be hashtag risk or winner. >> Ready? you really wasn't it. >> Wasn't it. because she just seems really awesome. with her. humble person and works really hard and what I was afraid of doing. she's stayed in one company, of different jobs. interesting. aware. however you want, but you need to understand that. in the beginning about how in a small, rectangular room. York, we went to Danville, Pennsylvania. from Jenna and Gabby. of passion in what they do. Chief Actuary at Geisinger Health named to see him because he's the  guy I aim to be. to do on this road trip is meet  someone who can be me. a field of study where you use much loss you're going to have. it's meant to kind of predict different disasters. about the Actuarial exams. it's next November. these exams, through. was like picking out the right outfit before and everything to make a good impression. about actuaries, what they do? about. and stuff but. as you were able to tell. how fine you guys? >> I have a question if he's student at the University of Connecticut, ladder with a couple Actuarial exams. explore the different fields, the career of an Actuary. more about what you're focused  on as Geisinger? is we sell health insurance products. the best quality healthcare to the people what healthcare costs are going  to be at for the historical information, look at that trend it forward to that  projection period. >> So with you my friend process too traits that you think are important >> You have to have I would almost say tenacity to get Going through the exam process is can be have a few times when you don't pass exams process. I can tell you in my own exam process, the time. So it was certainly not an easy But one that I think in the end was worthwhile. different and have that rare and valuable skill. mistakes and the whole course of taking all of them. yourself back up when you  happened to fail? to important things you can do in life. mean you're exams, or unable to kind of go  beyond measure of an individual is not really well. And when they're at the high point of been put down and bit. And, I really have a lot of respect for themselves off, get up, and then succeed. And you're not necessarily going to this is absolutely the job of my dreams. purpose. easy. kind of mature. opportunities to >> Are there any mistakes or anything, right away? And you kept making them? mistakes. >> Okay. got to look in A poor decision where you learn isn't necessarily a bad thing. to risk, allows you to grow. yourself off There's growth opportunities that are so There's a lot of things that will happen in your careers control. control is so important it's It's thinking about things that you can control. everything else happen. hear from through difficult experiences, right now, is kind of  discouraging. something that At the same time, that I'm scared of being in. north and a little to the west  and hit Niagara falls have been awesome, I've taken in a lot. every time. great, thats my new favorite much experience of putting  myself in situations that maybe I think coming on this Driving from the East to the West Coast of  to before. I was definitely putting myself outside Hopefully, this will be the start of me person. [MUSIC] some nature. ultimate nature attraction in the US. boat and drive towards the falls. up, take some pictures, go on a boat ride, and then come back. which is where you get drenched. tighten it really tight under my chin so get down. like no hood, no hood, put  your hood down. couldn't open my mouth. because she got literally  drenched. responsible. different and we have different roles. she's here to experience everything so crew. forward with all three of us, and holds us together. entertaining person. people I think I've ever met. he's really funny. guy. everyone is expected to conform. loose guy. we're about to interview David Shotts. insurance. [MUSIC] David Shotts did the insurance for. we looked like a little family. Ascend Insurance Brokerage. the entertainment industry. music festivals, events security companies,  television and film. agency in that space. thing about what you do? the entertainment industry. get to go to music festivals. and say, hey hey, I need tickets to this and you were doing around our age,  we're all 21. musician, I was playing in a  band and having a lot of fun. insurance to be quite honest. accident. field. industry. this industry like you. kind of found out I was really good at it  and that sales  when I was selling skateboards to kids. just continued through my life. were pretty tough on me. everything, to really learn  risk management. sitting there going, is this  what I want to do for had a big question mark like I  don't know. don't really want to do the  corporate thing anymore enjoying this industry and  enjoying this business. that I enjoy personally to enjoy this industry. a person identified all right, all day. memorable risk that you took,  like a big dive. industry [LAUGH]. >> You're not going to accomplish anything of risk, caution to the wind and just go for it. started by rolling the dice,  taking a risk, right? ready made situation where to the castle if you will. I don't think I want to do this. business. are going to watch this are going to have a negative  they're going to think it's really boring. before you worked in the industry and I would have totally agreed with that. the commercials that you see on television. people and I'll tell them what I do. didn't even know you could get insurance for that. beauty of the industry is that insurance is everywhere. home, auto, life. that focuses on extreme sports. fishing I know underwriters that specialize in that industry oyster. be really happy with what he did music and entertainment with the brokerage side. give up on being a broker in the insurance world to know that I can always find  something else within insurance. getting better and better. industry where the average age is 58. and I'm in my mid 30's. there looking to retire and that are going to come open. you're doing this at your age. I was, I mean I commend you all many different opportunities and like insuring for concerts. play. something that I really  admire about him. fast. almost halfway through. going to be done soon. this road want to do, but soak in a lot of their  advice. with me and it's good to have going into my last then starting my career after that. we've interviewed and has made me rethink insurance. must do this job forever kind of thing. the more I get to hear their stories, exited about what I'm doing. I just want to stay there, can. sure of what my next step is. 

Niagara Falls leaves the team in awe; then they attend a Chicago music festival with David Shotts, who helps insure concerts and events.

The World Is Your Oyster

confront risk face-to-face around unpredictable odds? of insurance, risk isn't just itself. Roadtrip Nation  country to uncover  improbability your profession. the risks behind to help people Risk & Reward. crybabies play this game.  Alain, you're out. crybabies play this game.  Alain, you're out.  Me? Are you serious? >> So Jenna bought this game called >> You have like a little Roulette, it jelly bean. >> But you don't know whether it's gonna a bad tasting flavor. >> It's the pink spotted? to figure it out. ones. >> It's corn, no, the worst. >> Wait, what did you get, >> But we had eggs this morning. >> [LAUGH] I knew Gabbie, before we even played. kill me. >> I'm gonna throw up. >> You have to. and then I understood how bad it was. three times times two cubed because the  chances of good or >> Just eat it. >> You got it again! laughed >> I can't even taste it anymore. so unlucky. >> We have less than ten days left. people, about what other people do. I didn't really know about  their job. credited the Lost Davis by essentially creating potential future warthquakes. issuing a policy, it's so about premium when you  can burn things up, shake things. sign me up. >> There's so many different out there like insuring  for concerts. oyster. What you want to do? home, auto, life. >> Don't just because,  yes, it is the insurance industry, an insurance policy day in and day out. opportunities. will change and it will  continue to do that. open to exploring it. hear from through >> A poor decision where  you learned necessarily a bad thing. personal and professional,  allows you to grow. happen in your career that are completely out of defining what you control is  so important. my degree technical background. interesting to see like  other jobs are available like more people skills for. what else is out there. >>Here in Denver, Colorado and she works in a company called Valen Analytics. on different types of risk. anything like that so that we didn't know about  that's out there for >> Hi, thank you. trip is because I'm kind of the first career that's been  offered to me, so and see what else is available in the industry and that suits me better. terrible mistake on the job. career. jobs. they're going right outta college. right out of [LAUGH] Let's be honest. you can blaze your own trail. here at Valen Analytics. models for property and them to better price and  select risks. the marketing campaigns across different >> So what made you be introduced in >> I kind of fell into it, tell you that. Purdue. industry for a while,  that was very stressful, Got my Master's in marketing. 2008 which was the worst  time to try to industry experience in anything. care company and so health insurance and started  to get more of in general. >> What would you say is your to be a professional can't paid for that, >> [LAUGH] industry that adopt the mindset  that we're selling. we're always experimenting, testing and learning fear of Failure if you come up with an idea and opportunity to continue learning and growing. about insurance, we're also  looking at the theme of risk. risk in your everyday life? or you're more risk averse? inherently risky in my career decisions actually than in some risky things career wise. no other job lined up. something that you should do. there. out here to Colorado, available cuz I was like, whoop, whoop. that I loved to try out  something new and my support network, and be a great decision. what kind of company I did want to work for I did not want to work for. into a job that I didn't love, and I was like, with this, and it kind of broke my spirit down hard. Then I took another  risk and left that job, and changes that I've done, move from psychology to business, I think that because I'm happy with where I found myself now. I love the company where I work. just being completely risk-averse because there's just learning what you  shouldn't do next time. >> So what final advice do you have for industry or starting our careers and then for advice a while back. He said you should focus on earning  the job  on to the job that you want. kind of backawards. about it, you should master what you're currently doing on making the most of what you have already. always have their eye on that next thing, but to earn that next thing? mastered where you are now? focused on climbing the ladder so what I'm doing, and that I'm constantly growing and things, to learn new things. mistakes. to try it out. To learn what  you like, Learn what you should do, learn  what you definitely should  never do again. was just taking the first job that was that I was gonna have to maybe not enjoy it and that'd be really sad. if you do a job and you don't really enjoy it, so that's good to hear. advice. much. >> Right, exactly. your stay in >> Yeah, we will. >> I've seen indoor rock climbing, but expect. >> Good job Alain. risky. careful. >> That's all I wanted to do. it was so worth it. up, you got this. equipment, there's no ropes or anything to catch quite risky. >> So close, so close. time that I did, I felt like I had achieved something. much experience of signing myself up for then doing it anyway and a lot of fun. airport in London when I was like, my God, on this plane now. to Salt Lake City. Cameron Allen. >> Who is a broker at Veracity Insurance. activities and >> Zip line companies, the rock climbing companies, and that can be from the actual operation manufacturing the equipment for all those. bit about your childhood, what you liked to do and what you like to do now? around it just wasn't a lifestyle for the future. my family the way I wanted it to, so all the time, camped overnight, standpoint even till today, so included outdoors. and sports. it's something that I really I do a lot of insurance for >> What initially I guess appealed to it a chance, I guess? outdoors, operations provide insurance and standpoint. throughout the past 15 or so industry. because of the love that I have for what I do. fun passion. their business is actually running or company or they provide hiking  tours or climbing tours and of fun to be able to have  those types of conversations, side of it. anything else. >> We're gonna go zip lining later. to make zip lining more safe and >> I think the involvement of the inspections that are being  done are key. training that takes place within these operations to employees are being safe. interesting because is an activity safe? there's no risk there? activity within the outdoor industry, risk. >> When he goes with his family hiking or stuff, he knows all the risks, so that I do in certain situations, different way. >> But just because I see things within scares me, right, I'm still up for adventure 100%. single day. single and you don't enjoy it, life. passions. risk. >> Zip lining was, time. beginning. off and kind of let yourself loose. good? To see someone do it first. two more people do it. I felt a little more  comfortable going down. it was more like, it was very safe. like what was holding me back  in my own mind. anything about what I'm trying to be an experience with it. lesson to have over the course  of my career. get to the edge and be teetering on the edge, the guy who worked there was  like, 'Okay, go' with it kind of thing. one, we were like okay, this is like a lot of fun. school. I don't like to lose. at anything in my life. so I wouldn't have failure. fear of failure scares me. about all the interviews we've had. away from each one and afraid to try new things. their career, and they're still doing that so a good reward with it and so to keep an open mind, trying career and not just saying, no, that's not for me. that. which way you can be turned down, email, wondered, that I should be doing? a niche. outwork people, I'm gonna stay longer, belief, stick with it, you're gonna do it. opportunities we actually have, take much advantage of it. realize how awesome it is, jump in! pool, find out if you swim. >> Hi, I'm Jenna. >> Chuck.m Jenna. father, and complained. birthday [LAUGH] says, I have some advice for you. he's never given me any direct advice. you really do control. years, and used me as an outsource manager. a tremendous amount of risk in my career, had a comfortable life. and then I went to Wall Street, for God's sake. was making hundreds of  thousands of dollars a family in Texas to start a hedge fund. be out of my mind. time. to do. development, wealth, opportunity. the world on a risk basis. someone? >> Yeah. done so >> Yeah, that's too bad. bad, >> No, no, no. >> Yeah. >> Yeah. for me, >> In high school, did I feel like I'd failed? gone through life and have not failed. failure, because seeing what value in knowing what does work. people react when things are failing because they don't rosy. lessons to >> You're to a point where if you're like, so what? what? what? >> The truth is the successes don't the failures don't mean too much. are my family and my friends, >> That would be terrible, >> [LAUGH] would find out is you're still  as smart as were the day  before.   background, yeah, I just can't believe it. right, you still have to play. can't do something or something, or I could never do that. how high up is, my wheels start turning more and more. gonna be done soon. gonna end. all the interviews we  have left, too. where I'm like, I miss my family. family, but I don't wanna go home. creep up really quickly. much to learn most out of it. 

Feeling emboldened to embrace more risk, the roadtrippers try out rock climbing and zip lining, and bond over a high-stakes board game.

What Are The Odds?

confront risk face-to-face around unpredictable odds? of insurance, risk isn't just itself. Roadtrip Nation  country to uncover  improbability your profession. the risks behind to help people Risk & Reward. of me posing on these rocks? face. [LAUGH] I can't with you. drive from Salt Lake City to California. were gonna be driving the RV for a long distance, so >> We had a really long 600-mile drive from Salt Lake City to California. were gonna be driving the RV for a long distance, so like, we want our turn to drive. easy, one long drive from Boston to California. you're just kind of on the other side of the country. we are going white water rafting. though, just beware. jacket I'll be fine. Be aware of the risk. get pretty like crazy out there and everything and And he was like, no it's pretty serious. am not a good swimmer at all. if I got thrown out of the raft, river. of leading the boat and so else had to go off of. they were just not in sync at all. motion going I'm like into it, beat. like, we're not in time we're  not in time. too much. of fixed things, like counting  beats for us, so we were in  time. were like, that felt good. same time and are literally like a family. start to understand each other's strengths and weaknesses all just pitch together and everybody, kind of work with any problems we had. we are like siblings. biological siblings, but sisters, which is really nice, I like it. together really well. it's very bitter sweet. day, you're a team. of doing interviews and amazing leaders  within the insurance industry. like, my god, is this the last day? all gonna be together as a group. and we're in San Francisco. Kate Sampson VP of  Risk Solution at Lyft. >> Hi! that was first on board with ride sharing everything, and of it. that sounds like so fun. we'll go downstairs. thing. here at Lyft and experience in the industry. I had an internship between my junior and me a job. as you did where I said, first thing? first thing and it was the best decision I made. to what you, perhaps, did your  degree in that and of how you felt going into the industry. political science double major. do. get an internship. fair happening on campus. lined up to talk to the insurance broker, so lo and selected for the internship and ended up when I left, the role as an account executive which was commercial insurance. be stuck in the I am, but more I realize that you can move around and first decision you made is a bad one. your first job is highly  unlikely be your last job. I probably went into it at that time as, better, I should have my whole career here. that the most successful very varied steps along the way. step that was gonna give me some insight into what my learning opportunities and yourself. risk. risky are you as a person in your personal life? a risk manager. I jump off something board into a pool, all those things like that. had built for many many years to the time when I came to Lyft, the company it is today. risky. the way. sharing, there was a lot of news about Lyft and Uber. an industry was going to survive? companies, they didn't wanna do all didn't work out, so there was a lot of pressure. like what do you think are important to be in the insurance industry? someone who is a risk taker, themselves, shouldn't be what you want  as a risk manager, willing to take risks. fearless, problems, is not afraid to speak up and a historical bias in the industry. potentially, has to say no a lot, to be followed with, but we can do this. attitude is important. each of these roles that you have, on your knowledge base. adaptable to many different things that you're not even at an insure tech-type  company that we that list is autonomous cars. dealer and buy a car, until you show that you have insurance. robot cars driving around, that the auto manufacturers put into it. technology companies put into it, and it that a network like Lyft might provide. accident it's gonna change everything, and exactly what happened in an accident, representative. he said, she said, situation. done one way in insurance for 25 years, or the way of the future. insurance at the right time for that. Lyft without swag. not- like, like, took the first job that was offered to her. matter how long I work for the company I work for, a valuable experience. something more innovative, of driving a blimp. wow, there that have that kind of  mindset, that was cool. insurance. like, well, maybe there's something out there for me. >>See ya, yeah. and less like, scared of risk, and with risk and stuff. carried with me. with my hero, he specializes in finance, it, cuz it's the last one. be a good one. >> One, two, three. >> Do it again. >> Why do we keep missing? >> My god. >> My name is Mehir Desai, Business School and Harvard Law School. In Hong Kong, and then we  moved to New Jersey. and I had this kind of, moment. jobs, and consulting and banking. you just take the  cocktail party test. you have to introduce yourself,  and you get to say, I'm a consultant. which one do you like better? choices. >> So, I went to India for a year, and PhD. unconventional choice as somebody coming out of worst that could happen? every year, for the last 20 years, so am. economics is, it's kind of linked to the insurance you don't work directly in it. the insurance industry. see it as really boring, like, going on, so what's your opinion on it? the core of economics,  it's really everything. mean, the most boring thing in the world, right? really intellectually challenging field, harder than a lot of other things. theory, like, it's kind of interesting questions, really different things in a really interesting way. because everything works because of risk aversion, recently finished, the first chapter, risk. everything, to human beings lives. about your book, when you said that, the significance of geography. cuz I feel like I don't have the right purpose for industry. near Hartford, the insurance capital. >>Sure. of, you know, where I live, as much as I can. there's so many different opportunities outside of the state to first, block out the noise of the world. around you who are saying, the hot, that, just go block all that out. you think about yourself, is you have to look at your past. activities that make you happy, but introspection. this problem is to go  experience the world. Do it in  as many ways as you can. There's a lot of things about  geography that matter. they kind of crawl into their shell, and I'm going to figure out my life. looking at myself, that's like, story. invest in new experiences than over invest. cuz like, of my personality, I guess. if you told me to just like, dive in, what about the plan, where am I gonna stay, all that stuff. do you have any advice for that, or? have a lot of safety nets  in your life. you're a smart thoughtful person. be like the best safety net in the world, a loving family, you have like, world. you, and then finally, you can make mistakes, and you'll be fine. worried about these things, is the cost of mistakes are really high. mistakes for you are really low, they're like minuscule. people are like, I'll just go back home. home but I'm willing to just go back home, you want to be as fast as you can. people, you're gonna be around things. and you can't access those  opportunities from back home. to go. you have like nothing to lose, you don't go back to a safe space. from there, I think what's happened to me in the last tried to take risks. I wrote a book, school. in each of those cases, it may not sound like and professionally, it felt risky. a book. we learn how to do anything. situation where you are at risk. perhaps, didn't pay off? probably should of taken more. if anything. this question which is, asked this question which is, somebody asked me, so missed? well you're doing something wrong. >> And the logic, of course, flight, of time early at airports. flights. >> If I talk to my mother about that she's  >>That's the way you live your life. miss a flight once in a while. couple of hours and then you go the next day, or never miss a flight, doing something wrong. way too early every time and you're wasting time there. >>There is an optimal number of flights to miss. we should be making. you should be more aggressive. you're only feeling 50% of the time.hould be more aggressive. you're only feeling 50% of the time. missed? >>So since then, I've probably missed five or six. >>I wonder what music they'll use. It'll be us, voice over. >> Yeah. our cross-country trip. same time. for another week, or a month, or year. experience that  interviews. of people we've met. But not enough. quote unquote failures. a tremendous value in knowing  what does work.  work. insurance because yes, it is the insurance industry, an insurance policy day in and day out. opportunities. static. want to do insurance, you know I'm pretty sure, and like, yeah, no, I'm really sure. great people. away from her with being a risk manager was that she is so not like me, but the way  she was describing it, that sounds like so much fun. and you get to say that you're a part of that. sure I want to be a risk manager. my family, go on this road trip. awesome reward in the end. I got a big reward. sound anyway. >> [LAUGH] professor always says, but I just like, love it. you have to tell everyone. they will tell you. actuary and being an actuary in the end, but just all the other possibilities you can have. music festivals you got to get music festivals, touring artists, event safety, get to go to music festivals. of the industry, is that insurance is everywhere. auto, life. I wanted to see, the different  kinds of people, and profession fit their lifestyle. actuary, I think being an  actuary does fit my life style  well. I'm gonna start studying. career I have in the future kind of embodies this  scare you - you'll surprise  yourself. luck. had nearly as much fun if they hadn't been here. [MUSIC] >>Thank you. trip for me. that certain things were very risky, and very risky. have all these safety nets and  a lot of things  I perceive actually that much I could lose from doing them. try out the job that I've been offered. impression that women were under represented in many powerful innovative women. have literally inspired me every single day. with amazing people. we had together. if you weren't singing  at some point. before. beings is the problem of an insurance company, everywhere and you gotta make sense of it. that? in the randomness. >> Kizuna. the other roadtrippers. companies. chaos in the world, experience it. an individual, just invest in yourself, the world. 

The journey comes to a close with Lyft’s Kate Sampson and Harvard professor Mihir Desai talking risk-taking and challenging the status quo.

Look For The Risk-Takers

Every career contains an element of uncertainty. But for insurance professionals, risk isn’t just a sidelong possibility: it’s the job itself. That’s why this summer, with the support of Travelers, Roadtrip Nation is sending three young adults interested in the insurance industry on a road trip to uncover what it’s like to make improbability your profession. They’ll talk to people across the country to explore the risks behind betting against unknown odds—and the rewards of being able to help people when they need it most. Follow the road‐trippers’ journey below, then stay tuned to watch the series when it premieres.

Insurance Roadtrip

STOPS & INTERVIEWS

STOPS & INTERVIEWS

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