>>What does it look like to confront risk face-to-face every day?

To build a career-and a life- around unpredictable odds?

For professionals in the world of insurance, risk isn't just a possibility: it's the job itself.

That's why this summer, Roadtrip Nation sent three people across the country to uncover what it's like to make improbability your profession.

They hit the road to explore the risks behind betting against unknown odds and the rewards of being able to help people when they need it most.

This is Roadtrip Nation Risk & Reward.

Do you wanna get a picture of me posing on these rocks?

>> I literally can't see your face.

Okay, I'm taking it anyway.

>> [LAUGH] Just do it.

>> That could be anyone.

>> That's beautiful [LAUGH] I can't with you.

[MUSIC] >> Let's get going.

[MUSIC] >> We had a really long 600-mile drive from Salt Lake City to California.

I knew it was the last time we were gonna be driving the RV for a long distance, so I think all of us were kind of like, we want our turn to drive.

[MUSIC] >> I almost thought it was too easy, one long drive from Boston to California.

And then, before you knew it, you're just kind of on the other side of the country.

[MUSIC] >>We're in California, we are going white water rafting.

>> I've seen other boats flip, though, just beware.

>> As long as I have a life jacket I'll be fine.

>> Don't do that.

>>Yeah, I'm just saying.

Be aware of the risk.

>> Alain was like, yeah, it can get pretty like crazy out there and everything and we are like wait.

what?

And he was like, no it's pretty serious.

>> I was nervous because I am not a good swimmer at all.

I was just saying like, my God, if I got thrown out of the raft, till I'm just stuck in the river.

[LAUGH] And I can't save myself.

[MUSIC] >> Me and Gaby had the pleasure of leading the boat and so our strokes is what everyone else had to go off of.

>> Yeah, they were just not in sync at all.

>> And I would have a whole motion going I'm like into it, like my whole body is like on a beat.

>>Jenna kept shouting at me like, we're not in time we're not in time.

>> I was just like.

Like, this is just too amusing, too much.

>>Alain, was the one who kind of fixed things, like counting beats for us, so we were in time.

>> One, two.

>> Once we like go it going we were like, that felt good.

Like we were doing it at the same time and it was cool because we are literally like a family.

We're siblings and we could like start to understand each other's strengths and weaknesses It's kind of amazing how we all just pitch together and find the right balance between everybody, kind of work with any problems we had.

>> In our relationship, we are like siblings.

They're nothing like my actual biological siblings, but we get on like brothers and sisters, which is really nice, I like it.

We all started working together really well.

Now we all have to go home.

>> It's already the last day and it's very bitter sweet.

>> You're with your people every day, you're a team.

You get in to this routine of doing interviews and getting, to meet with these amazing leaders within the insurance industry.

>> I woke up this morning, I was like, my god, is this the last day?

This is like the last time we're all gonna be together as a group.

[MUSIC] >>It's the 26th day of the trip and we're in San Francisco.

>> And we're about to interview Kate Sampson VP of Risk Solution at Lyft.

[MUSIC] >> Meeting her, she was awesome.

>> Hello.

>> Hi!

>> Nice to meet you.

>>She was one of the people that was first on board with ride sharing kind of like creating it and everything, and figuring out the different risks of it.

Yeah, I'm like, oh my god, that sounds like so fun.

>> All right, so, we'll go downstairs.

>> What.

>> Oh my God, this is the coolest thing.

It's really heavy.

>> It's so cool.

>> My name is Kate Sampson.

I am the VP of Risk Solutions here at Lyft and I have 22 years of experience in the industry.

And very similar to Gaby, I had an internship between my junior and senior year.

And my senior year, they offered me a job.

I felt exactly the same as you did where I said, am I really just taking the first thing?

And I really did just take the first thing and it was the best decision I made.

[MUSIC] Could you kind of take us back to what you, perhaps, did your degree in that and what you did after that and kind of how you felt going into the industry.

>> So, I was an economics and political science double major.

I didn't know what I wanted to do.

I knew I probably should get an internship.

It was my junior year.

And there was an internship fair happening on campus.

There weren't a lot of people lined up to talk to the insurance broker, so lo and behold, I ended up getting selected for the internship and ended up when I left, they offered me a job and I took the role as an account executive which was essentially a salesperson for commercial insurance.

>> I worry that I'm gonna be stuck in the I am, but the more people I talk to the more I realize that you can move around and that doesn't mean that that first decision you made is a bad one.

>>First, I will tell you your first job is highly unlikely be your last job.

When I took that first job, I probably went into it at that time as, I better be successful, and I better, I should have my whole career here.

But quickly I started to realize that the most successful people I saw in my mentors had very varied steps along the way.

And I recognized, this was a step that was gonna give me some insight into what my what my next role would be.

So it never goes away.

And embrace all of them as learning opportunities and things that you find out about yourself.

>> So insurance is all about risk.

And we are kind of wondering how risky are you as a person in your personal life?

>> I think I am pretty risky for a risk manager.

Every year, I try to make sure I jump off something skiing, do a flip off a diving board into a pool, all those things like that.

Leaving a great career that I had built for many many years to come try a start-up where at the time when I came to Lyft, it was certainly not the company it is today.

It was much smaller, it was very risky.

I hit a lot of brick walls on the way.

And if you think about ride sharing, there was a period of time where there was a lot of news about Lyft and Uber.

And who knew if ride sharing as an industry was going to survive?

So that scared insurance companies, they didn't wanna do all this work if the regulations didn't work out, so there was a lot of pressure.

>> This might turn general, but like what do you think are important character traits that you need to be in the insurance industry?

>> I'm looking for someone who is a risk taker, themselves, which seems almost like it shouldn't be what you want as a risk manager, but I want someone who's willing to take risks.

I'm looking for someone who's fearless, that is not afraid to tackle problems, is not afraid to speak up and challenge what might be a historical bias in the industry.

And a risk manager inherently, potentially, has to say no a lot, but if I have to say no, it has to be followed with, but we can do this.

Having that kind of can-do attitude is important.

>> Hence, Risk Solutions.

>>Hence, risk solutions, each of these roles that you have, will continue to build on your knowledge base.

And allow you to be very adaptable to many different things that you're not even thinking about right now.

You all three could be working at an insure tech-type company that we don't even know exists yet.

And what's always at the top of that list is autonomous cars.

So, if you go into an auto dealer and buy a car, you can't take that off the lot until you show that you have insurance.

And now we're going to have robot cars driving around, that are powered by hardware that the auto manufacturers put into it.

Operating systems that technology companies put into it, and they may still have a driver in it that a network like Lyft might provide.

So when that car gets into an accident it's gonna change everything, and when you think about robot cars.

They may be able to tell us exactly what happened in an accident, versus today a claims representative.

Trying to figure it out in a he said, she said, situation.

So, just because something was done one way in insurance for 25 years, doesn't mean it's the right way, or the way of the future.

And at the end of the day, you're definitely entering insurance at the right time for that.

>>It wouldn't be a visit to Lyft without swag.

>> Well, this one is like, I did not- >> She was kind of like me, like, she graduated, took the first job that was offered to her.

It made me realize that no matter how long I work for the company I work for, it's still going to be a valuable experience.

>> The idea of working with something more innovative, like quantifying the risk of driving a blimp.

When I heard that, they're like, wow, there's insurance companies out there that have that kind of mindset, that was cool.

>> I work in commercial insurance.

>> Risk managers to me, are like, amazing people, I'm like, okay, well, maybe there's something out there for me.

>>Thank you.

>>See ya, yeah.

>> I need to be more open-minded and less like, scared of risk, and she was super open-minded with risk and stuff.

So that like, really carried with me.

[MUSIC] >> So, the last interview was with my hero, he specializes in finance, I almost feel nervous for it, cuz it's the last one.

And like, I want it to be a good one.

>> [LAUGH] >> One, two, three.

>> [LAUGH] >> Do it again.

>> One, two, three.

>> [SOUND] >> Why do we keep missing?

>> One, two, three.

[SOUND] >> My god.

>> [LAUGH] >> My name is Mehir Desai, I'm a Professor at Harvard Business School and Harvard Law School.

I was born in Bombay, and raised In Hong Kong, and then we moved to New Jersey.

And I went to business school, and I had this kind of, a little bit of an epiphany moment.

Where I was interviewing for jobs, and I was trying to decide between consulting and banking.

And this guy said to me, well, it's really simple, you just take the cocktail party test.

You go to a cocktail party, and you have to introduce yourself, and you get to say, I'm a Banker.

Or you get to say I'm a consultant.

And he said which one do you like better?

And I said, I don't like the choices.

>> [LAUGH] >> So, I went to India for a year, and then I came back and I did a PhD.

And that was a kind of unconventional choice as somebody coming out of business school.

But I figured what was the worst that could happen?

And I kept making that decision every year, for the last 20 years, so that's how I ended up where I am.

[MUSIC] >> So I was wondering, like economics is, it's kind of linked to the insurance industry, but you don't work directly in it.

So what is your view of the insurance industry.

Because a lot of young people see it as really boring, like, there's nothing interesting going on, so what's your opinion on it?

>> So, insurance is actually, the core of economics, it's really everything.

And in fact, you're right, I mean, people think insurance is like the most boring thing in the world, right?

But insurance is actually a really intellectually challenging field, intellectually it's hard, harder than a lot of other things.

But there's also a little bit of theory, like, it's kind of interesting questions, about human behavior.

It captures a lot of really different things in a really interesting way.

And it's the core of finance, because everything works because of risk aversion, risk has got to get priced.

So in writing this book that I recently finished, the first chapter, I made it about insurance and risk.

Because it is so core to everything, to human beings lives.

>> I was reading a little bit about your book, when you said that, we underestimate the significance of geography.

It really like struck me hard, cuz I feel like I don't have the right purpose for going into the insurance industry.

And growing up in Connecticut, near Hartford, which is considered like, the insurance capital.

>>Sure.

>>I would love to take advantage of, you know, where I live, as much as I can.

But at the same time, there's so many different opportunities outside of the state >> I think it's really important to first, block out the noise of the world.

Cuz there's a lot of people around you who are saying, the hot, sexy thing to go do is this or that, just go block all that out.

Because it can corrupt what you think about yourself, The second, is you have to look at your past.

Think about the kinds of activities that make you happy, but I'm not a huge fan of introspection.

I think the way to figure out this problem is to go experience the world.

Do it in as many ways as you can.

Geography is destiny.

There's a lot of things about geography that matter.

The mistake most people make is, they kind of crawl into their shell, and they're like, I'm going to figure out my life.

By spending a lot of time looking at myself, that's like, that's half, a quarter of the story.

You're more likely to under invest in new experiences than over invest.

>> I guess going off of that, cuz like, that's like the opposite of my personality, I guess.

Like I like have more fears of if you told me to just like, dive in, go here go there.

I'm like, what about the plan, where am I gonna stay, all that stuff.

So I guess like, do you have any advice for me on like how I could get over that, or?

>> Well, I mean, I think you have a lot of safety nets in your life.

Number one, you're a smart thoughtful person.

So your human capital is gonna be like the best safety net in the world, you're gonna land on your feet.

Number two, if you come from a loving family, you have like, the best safety net in the world.

They're gonna be there for you, and then finally, you're incredibly young, and so you can make mistakes, and you'll be fine.

So when you say that you're worried about these things, implicity what you're saying, is the cost of mistakes are really high.

And the reality is the cost of mistakes for you are really low, they're like minuscule.

When you start out, some people are like, I'll just go back home.

I don't really wanna end up at home but I'm willing to just go back home, That's a bad idea.

Go to where you want to be as fast as you can.

Because you're gonna meet people, you're gonna be around things.

Opportunities are gonna open up, and you can't access those opportunities from back home.

You kinda just got to go.

And when you're young, you have like nothing to lose, that's the way forward, you don't go back to a safe space.

And then try to figure it out from there, I think what's happened to me in the last several years, is I've again, tried to take risks.

So I've built an online course, I wrote a book, I started teaching at the law school.

I'm not a lawyer but it's like, in each of those cases, it may not sound like sky diving, but intellectually and professionally, it felt risky.

Like I didn't know how to write a book.

I didn't know how to teach law.

That is ultiamtely the only way we learn how to do anything.

You put yourself in the situation where you are at risk.

>> Were there any risks that, perhaps, didn't pay off?

>> I don't think so.

And maybe that's glib, but I think that the reality is I probably should of taken more.

I probably didn't fail enough, if anything.

A lot of economist talk about this question which is, I remember the first time I was asked this question which is, somebody asked me, so how many flights have you missed?

And I quite proudly said, none.

And then they said, well you're doing something wrong.

[LAUGH] >> And the logic, of course, is if you've never missed a flight, that means you're spending a lot of time early at airports.

You should optimally miss some flights.

>> [LAUGH] >> If I talk to my mother about that she's like, you never miss a flight.

>> That's how I am.

>>That's the way you live your life.

>> [LAUGH] [LAUGHS] It's ok to miss a flight once in a while.

It's perfectly fine, you waste a couple of hours and then you go the next day, or whatever it is.

But if you never miss a flight, then you're systematically doing something wrong.

You're getting to the airport way too early every time and you're wasting time there.

>> Interesting.

>>There is an optimal number of flights to miss.

There are lots of mistakes we should be making.

Should be feeling more, you should be more aggressive.

You're doing something wrong if you're only feeling 50% of the time.

>> So how many flights have you missed?

>>So since then, I've probably missed five or six.

And it's perfectly fine.

>> Okay.

[MUSIC] >> Oh, my Lord, it's cold.

[LAUGH] >>I wonder what music they'll use.

>>I think it'll be voice overs.

It'll be us, voice over.

>> I think they use some though.

>> Do they?

>> Yeah.

>>We're at the end point of our cross-country trip.

>> It's kind of sad.

>> I'm not ready to leave.

I'm excited to go home at the same time.

But I'd love to do this, I guess for another week, or a month, or year.

I don't want to go to work.

I'm just kidding!

>> I don't there is any experience that you can get that matches this.

You get to see a whole country.

>> I do reflect a lot on the interviews.

So many different kinds of people we've met.

>> Sprinklers are good.

But not enough.

[MUSIC] >>Don't think of any mistakes or quote unquote failures.

Those are learning experiences.

Be fearless out there.

>> Seeing what doesn't work is a tremendous value in knowing what does work.

>> Value in knowing what does work.

>> Don't just think of it as insurance because yes, it is the insurance industry, but I'm not living my day in an insurance policy day in and day out.

There really are other opportunities.

It's not going to remain static.

I came in with like, yeah, I want to do insurance, you know I'm pretty sure, and now after the road trip, I'm like, yeah, no, I'm really sure.

Just like meeting with these great people.

I really liked Kate.

The biggest thing like I took away from her with being a risk manager was that she doesn't say no to things which is so not like me, but the way she was describing it, I'm like, oh my God, that sounds like so much fun.

And like now, look where you are and you get to say that you're a part of that.

I'm like, okay, now for sure I want to be a risk manager.

It was like a big risk to leave my family, go on this road trip.

It was like a really awesome reward in the end.

Like I took a big risk and I got a big reward.

[MUSIC] They're not going to use the sound anyway.

>> No, but- >> [LAUGH] [MUSIC] >> Okay, this marker sucks.

It's a quote my professor always says, but he got it from someone else, but I just like, love it.

[MUSIC] When you are good at something you have to tell everyone.

When you are great at something they will tell you.

Oh my god, I'm out of breath.

>> I can see myself as an actuary and I can also see myself not being an actuary in the end, but it's exciting thinking about just all the other possibilities you can have.

If what you like to do is go to music festivals you got to get a job like David Shotts.

[MUSIC] >> We work with music venues, music festivals, touring artists, event safety, event security companies.

I mean it's kind of cool I get to go to music festivals.

I think it's kind of the beauty of the industry, is that insurance is everywhere.

It doesn't just stop with home, auto, life.

>> I guess that's really what I wanted to see, the different kinds of people, and the way that they made their profession fit their lifestyle.

Going back to me being an actuary, I think being an actuary does fit my life style well.

I'm gonna go back and I'm gonna start studying.

You just gotta kind of dive in.

I simply wish that the career I have in the future kind of embodies this experience.

[MUSIC] >> Say yes to things that scare you - you'll surprise yourself.

And remember to make your own luck.

>> [LAUGH] >> I don't think I would have had nearly as much fun if they hadn't been here.

>> Everything's fine.

>> Everything's not fine!

[MUSIC] >>Let me help you.

>>Thank you.

[MUSIC] >>They have like made the trip for me.

[MUSIC] Before I came here, I thought that certain things were very risky, and actually in fact, they're not very risky.

Like with what Mihir said we have all these safety nets and a lot of things I perceive to be risky like there's not actually that much I could lose from doing them.

So yeah, I'm definitely going to try out the job that I've been offered.

I think I was under the impression that women were under represented in the industry, but I've met so many powerful innovative women.

I have interviewed people that have literally inspired me every single day.

And I got to do all that with amazing people.

[SINGING] All the times we had together.

>> It wouldn't be a normal day if you weren't singing at some point.

I've never heard this song before.

>>We're really like a family.

>> Now we all have to go home.

>> The problem for most human beings is the problem of an insurance company, which is there's chaos everywhere and you gotta make sense of it.

How do insurance companies do that?

They look for the patterns like in the randomness.

>> Kizuna.

>> What does it mean?

>> It means bond.

[MUSIC] >>That is my message to the other roadtrippers.

>>We are all insurance companies.

[MUSIC] You see all this randomness and chaos in the world, the only way to solve is to experience it.

That's what you have to do as an individual, just invest in yourself, never stop investing.

Go out and experience the world.

[MUSIC] To learn more about how to get involved, or to watch interviews from the road visit roadtripnation.com