>>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 not let wimps or crybabies play this game.

Alain, you're out.

Me?

Are you serious?

You two [CROSSTALK] >> So Jenna bought this game called Bean Boozled.

>> You have like a little Roulette, it points to a certain color of a jelly bean.

>> But you don't know whether it's gonna be like a good tasting flavor or a bad tasting flavor.

So this pink spotted one.

>> It's the pink spotted?

>> What is it?

>> I think it is stinky socks.

>> You like it?

>> No.

>> [LAUGH] >>It just took a while to figure it out.

>> [LAUGH] >> Caramel corn or moldy cheese.

[MUSIC] >> I'm hoping we both got bad ones.

>> It's corn, no, it took a very dramatic turn for the worst.

This is really disgusting.

[LAUGH] >> Wait, what did you get, rotten- [LAUGH].

>> But we had eggs this morning.

I'm gonna be sick.

>> [LAUGH] I knew Gabbie, I said it from the beginning before we even played.

Gabbie, your reactions are gonna kill me.

No [LAUGH].

>> Rotten egg, rotten egg.

>> I'm gonna throw up.

[LAUGH] Sorry, I can't do it.

I can't do it.

>> You have to.

>> She got it two times in a row and then I went, and I got it, and then I understood how bad it was.

>> [INAUDIBLE] worst one.

>> She won again.

>> Her chances of landing that three times in a row is one over eight cubed times two cubed because the chances of good or bad flavor, right?

So that's 4,096.

>> Just eat it.

[LAUGH] >> You got it again!

>> I literally have never laughed that hard.

>> I can't even taste it anymore.

>> [LAUGH] No!

>> I don't know how you can be so unlucky.

>> [LAUGH] [MUSIC] >> Yeah.

>> We have less than ten days left.

>> Just meeting with these great people, I just really like finding more about what other people do.

>> Some of them I'm like, I know about your job.

Until I interview them, okay, I didn't really know about their job.

>> The industry that I guess I'm credited with inventing was to create the Lost Davis by essentially creating a model that could simulate potential future warthquakes.

It's so much more than just issuing a policy, it's so much more than just talking about premium when you can burn things up, when you can shoot things and shake things.

If that's what insurance is sign me up.

>> There's so many different opportunities and cool things out there like insuring for concerts.

>>The insurance world is your oyster.

What you want to do?

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

>> Don't just think of it as an 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.

The entire insurance industry will change and it will continue to do that.

So I would say just be open to exploring it.

>> It felt really assuring to hear from someone that's already gone through difficult experiences.

>> A poor decision where you learned a lot about yourself isn't necessarily a bad thing.

Opening yourself up to risk, personal and professional, allows you to grow.

There's a lot of things that'll happen in your career that are completely out of your control.

And really defining what you control is so important.

>>I don't really want to waste my degree cuz I come from a very technical background.

But I think it would be quite interesting to see like other jobs are available that maybe I can use, like more people skills for.

>> So be interesting to see what else is out there.

[MUSIC] >>Here in Denver, Colorado and it's the 17th day of the trip.

[MUSIC].

We interviewed Naomi DeMarco, she works in marketing for a company called Valen Analytics.

>> They like built models for insurance companies to take on different types of risk.

I've never even heard of anything like that so that's just like another thing that we didn't know about that's out there for insurance.

>> Hi >> Hello >> Hi, thank you.

>> Naomi.

Nice to meet you.

>> The reason I'm on this road trip is because I'm kind of concerned that I'm just taking the first career that's been offered to me, so I kind of want to look around and see what else is available in the industry and see if there might be something that suits me better.

>> You're 21 years old.

You get out of school at 22 or whatever, and you make some terrible mistake on the job.

It's not going to tank your career.

Some people are afraid to change jobs.

Some people are afraid that they're going to make the wrong decision right outta college.

Nobody makes great decisions right out of college.

[LAUGH] Let's be honest.

Everybody makes mistakes in their early days, but you can blaze your own trail.

[MUSIC] I am the Marketing Director here at Valen Analytics.

Our company builds predictive models for property and casualty companies that allow them to better price and select risks.

My role here is the execution of the marketing campaigns across different channels, so on our website, email, social media.

>> So what made you be introduced in the field of insurance?

>> I kind of fell into it, a lot of people may tell you that.

[LAUGH] I was in school at Purdue.

I was majoring in Psychology.

I worked in the mental health industry for a while, that was very stressful, very taxing.

It just didn't work out.

So I went back to school.

Got my Master's in marketing.

From there, I graduated in 2008 which was the worst time to try to come out of school with no industry experience in anything.

And found myself at a vision care company and so that's where I was licensed in health insurance and started to get more of an introduction into insurance in general.

>> What would you say is your favorite part about your job?

I think it's the learning.

[LAUGH] I always wanted to be a professional student as it turns out you can't paid for that, it's like negative pay.

>> [LAUGH] >> We are working with an industry that it's challenging to get them to adopt the mindset that we're selling.

We're always trying new things, we're always experimenting, testing and learning and there's not this crushing fear of Failure if you come up with an idea and it doesn't work.

Try a new idea.

That's okay.

That's what I like most is the opportunity to continue learning and growing.

>> So as this documentary is about insurance, we're also looking at the theme of risk.

How would you say you approach risk in your everyday life?

Are you quite a risky person, or you're more risk averse?

>> [LAUGH] I have some inherently dangerous hobbies, I think.

But I'm probably a little more risky in my career decisions actually than in general life.

And so I've done some risky things career wise.

quitting jobs when I had no other job lined up.

That's not a general rule of something that you should do.

But sometimes it's necessary.

And so I've taken some risks there.

So when I first moved out here to Colorado, I took the first job that was available cuz I was like, whoop, whoop.

I gotta a job!

Let's go, you know.

It was a big risk leaving a job that I loved to try out something new and move across the country without my support network, and that turned out not to be a great decision.

[LAUGH] I mean, it taught me what kind of company I did want to work for because that was a company I did not want to work for.

I come from a job that I loved into a job that I didn't love, and I was like, I don't even know how to cope with this, and it kind of broke my spirit down a little bit and so that was hard.

Then I took another risk and left that job, and went to find something else.

But I think making the career changes that I've done, going back to school, trying to move from psychology to business, I think that it's all been very rewarding because I'm happy with where I found myself now.

I like the work that I do, I love the company where I work.

I generally would not advise just being completely risk-averse because there's always some reward even if it's just learning what you shouldn't do next time.

[LAUGH] >> So what final advice do you have for us going into the insurance industry or starting our careers and then for other people as well?

>>So, somebody gave me some advice a while back.

He said you should focus on earning the job you have before trying to move on to the job that you want.

And I was like that seems kind of backawards.

But at the same time, think about it, you should master what you're currently doing and you should really be focused on making the most of what you have already.

Because I've met people who always have their eye on that next thing, but what are you doing now to earn that next thing?

How are you proving that you've mastered where you are now?

I've never really been super focused on climbing the ladder so much as making sure that I know what I'm doing, and that I'm constantly growing and constantly learning.

Don't be afraid to try new things, to learn new things.

Don't be afraid to make mistakes.

Don't be afraid to just try, to try it out.

To learn what you like, learn what you don't like.

Learn what you should do, learn what you definitely should never do again.

[LAUGH] [MUSIC] >> I've always worried that I was just taking the first job that was offered to me and I was worried that I was gonna have to maybe not enjoy it and then give up on it and that'd be really sad.

And she kind of said that even if you do a job and you don't really enjoy it, it's not a worthless experience, so that's good to hear.

>> Never stop learning, that is my biggest piece of advice.

I mean, you can never know too much.

>> Right, exactly.

>> That's not a thing.

>> [LAUGH] >> [LAUGH] Thanks so much.

>> Good luck.

>> Thank you very much.

>> You're welcome, of course.

>> Thank you.

>> Enjoy the rest of your stay in Colorado.

>> Yeah, we will.

[MUSIC] >> Can you give me the rubbish?

[MUSIC] >> Wait, where's my shoes?

[MUSIC] Found my shoes.

>> I've seen indoor rock climbing, but I wasn't really sure what to expect.

It's nothing like that at all.

>> Good job Alain.

>> It was very windy, it felt risky.

[MUSIC] >> Be careful, please be careful.

>> [MUSIC] >> [LAUGH] >> That's all I wanted to do.

>> It was a far hike up, it was so worth it.

[MUSIC] >> Reach up, reach all the way up, you got this.

[MUSIC] >> You're climbing without any equipment, there's no ropes or anything to catch you if you fall, so that was quite risky.

>> So close, so close.

[MUSIC] >> I really enjoyed it, every time that I did, I felt like I had achieved something.

Before the trip I hadn't had much experience of signing myself up for something that terrifies me and then doing it anyway and realizing that it's a lot of fun.

That's kind of how I felt at the airport in London when I was like, my God, I really do have to get on this plane now.

[LAUGH] [MUSIC] So today we're driving to Salt Lake City.

[MUSIC] [MUSIC] >> We're about to interview Cameron Allen.

>> Who is a broker at Veracity Insurance.

They specialize in outdoor activities and that kind of thing.

>> Zip line companies, the rock climbing companies, the river rafting companies, and that can be from the actual operation side to the people who are manufacturing the equipment for all those.

[MUSIC] >> Could you tell us a little bit about your childhood, what you liked to do and maybe how it connected to what you like to do now?

>> My childhood was really based around working on a farm, but it just wasn't a lifestyle for the future.

To be able to provide for my family the way I wanted it to, so I enjoyed working on the farm.

My dad and I used to go fishing all the time, camped overnight, fished the streams.

So from a childhood hobby standpoint even till today, so a lot of my hobbies included outdoors.

That was a lot of them, and sports.

So I've made it so it's something that I really enjoy from the standpoint of I do a lot of insurance for outdoor recreation companies.

>> What initially I guess appealed to you about insurance?

Why did you want to give it a chance, I guess?

>> It was the attraction to the outdoors, but also the focus on helping operations provide insurance and take care of them from that standpoint.

And that's been my primary focus throughout the past 15 or so years, is really the outdoor industry.

For me, it was a job, but then it fell into being a career because of the love that I have for what I do.

And so it turned into being a fun passion.

You talk to a company and their business is actually running or operating a river rafting company or they provide hiking tours or climbing tours and that sort of thing.

It's a lot of fun to be able to have those types of conversations, and also the adventure side of it.

I don't see myself doing anything else.

>> We're gonna go zip lining later.

What are the measures you take to make zip lining more safe and have less accidents?

>> I think the involvement of the equipment that's being used, the inspections that are being done are key.

Then also there's a lot of training that takes place within these operations to make sure that their employees are being safe.

The word safe is very interesting because is an activity safe?

Yes it is.

But does it mean that there's no risk there?

No, because every single activity within the outdoor industry, in my mind, there is a potential risk.

>> When he goes with his family hiking or goes to these zip lining and stuff, he knows all the risks, so that's what he's thinking about.

So that's kind of the things that I do in certain situations, always looking at them in a different way.

>> But just because I see things within the insurance industry that scares me, right, I'm still up for adventure 100%.

I enjoy coming to work every single day.

I enjoy the people I work with.

I think if you go to work every single and you don't enjoy it, you're not going to truly enjoy life.

So it comes back down to your passions.

Don't be afraid to take that risk.

>> Zip lining was, [MUSIC] Well, I mean it was my first time.

I was pretty shaky in the beginning.

It feels unnatural to just jump off and kind of let yourself loose.

>> Nervous at all or you feeling good?

>> A little bit of both.

I just felt like I needed To see someone do it first.

And then I needed to see two more people do it.

And then three more, then maybe I felt a little more comfortable going down.

And as soon as I did it, it was more like, it was very safe.

[MUSIC] >>It was really more just about like what was holding me back in my own mind.

Pretty okay, I feel fine.

[LAUGH] I can't conclude anything about what I'm trying to be until I actually have an experience with it.

Really gotta try it first.

That's something that is a good lesson to have over the course of my career.

[MUSIC] >> I thought like that I would get to the edge and be teetering on the edge, not being able to jump.

But once I was strapped in and the guy who worked there was like, 'Okay, go' I was like, just get on with it kind of thing.

[MUSIC] Once everyone got over the first one, we were like okay, this is like a lot of fun.

>> [INAUDIBLE] >> I played sports in high school.

I can get super competitive.

I don't like to fail, I don't like to lose.

[MUSIC] >>I've never like truly failed at anything in my life.

I've always played it safe, too, so I wouldn't have failure.

Within my career and stuff, fear of failure scares me.

I've just been trying to think about all the interviews we've had.

Everything that I've taken away from each one and they always said don't be afraid to try new things.

Some of them took risks within their career, and they're still doing that so obviously it was really good.

Risks that they took they had a good reward with it and so that's why I'm just trying to keep an open mind, trying different things that's in a career and not just saying, no, that's not for me.

I can't ever see myself doing that.

[MUSIC] >> I've been turned down every which way you can be turned down, email, phone, in person.

There were times where I wondered, is there something else that I should be doing?

I knew I was gonna have to have a niche.

And that niche is I'm gonna outwork people, I'm gonna stay longer, come in earlier.

But it's that drive, that self- belief, where I knew that if you just stick with it, you're gonna do it.

If you don't realize how much opportunities we actually have, then you're not gonna want to take much advantage of it.

But when you see and realize how awesome it is, jump in!

Jump into the deep end of the pool, find out if you swim.

[MUSIC] >> Hi.

>> Hi, I'm Jenna.

>> Chuck.

>>Hi, I'm Gabbie.

>> I was very close with my father, and he was a man of his generation.

Never explained, never complained.

And my father, on my 21st birthday [LAUGH] says, I have some advice for you.

My God, he's never given me any direct advice.

He says listen to me, work hard.

It's the one variable you really do control.

[MUSIC] My name's Jeff Devers.

I ran a hedge fund for 20 some years, and a number of insurance companies used me as an outsource manager.

First of all, I would say I took a tremendous amount of risk in my career, right?

I could've been a CPA.

I would've made decent dough and had a comfortable life.

But I went to business school, and then I went to Wall Street, for God's sake.

Who knew?

And then I quit a job where I was making hundreds of thousands of dollars to go to work for a family in Texas to start a hedge fund.

What are you, kidding?

I had to be out of my mind.

>> But it made sense at the time.

It seemed to be the right thing to do.

It seemed to be more fulfilling.

It would create greater personal development, wealth, opportunity.

It did all those things.

It made all the sense in the world on a risk basis.

>> So what do you say to someone?

I have a fear of failure.

>> Yeah.

>> Just because I have always done so well.

>> Yeah, that's too bad.

>> I don't know if that sounds bad, but whatever.

>> No, no, no.

I- >> Yeah.

You know what I'm saying?

>> Yeah.

>> So what advice would you have for me, then?

>> In high school, I wanted to be a doctor.

I started out pre-med.

That didn't work well for me.

[LAUGHS] When I changed out of pre med, did I feel like I'd failed?

Yes, but I can't imagine having gone through life and have not failed.

That would be terrible.

There's a lot to be learned from failure, because seeing what doesn't work is a tremendous value in knowing what does work.

And by the way, seeing how people react when things are failing because they don't act the same way when things are rosy.

So there's all sorts of great lessons to be learned from failure.

>> You're to a point where if something doesn't work out, you're like, so what?

But how do you get to that so what?

I don't know how to get to so what?

>> The truth is the successes don't mean too much, and the failures don't mean too much.

Truth is the things I care about are my family and my friends, and it's perspective.

If you failed a class- >> That would be terrible, right?

>> [LAUGH] >> My world would crumble.

[LAUGH] Yeah.

>> Right, and then what you would find out is you're still as smart as were the day before.

>> Your mom still loved you, your dog still loved you.

At your age, with your background, yeah, it's gonna feel like, my god, I just can't believe it.

You just need more rejection.

When you get dealt bad cards, right, you still have to play.

Do not self limit, okay?

Don't tell yourself you can't do something or it's inappropriate to try to do something, or I could never do that.

I mean, you guys don't know how high up is, so don't limit yourself.

Each interview, I just feel like my wheels start turning more and more.

What am I gonna do with my life?

It's crazy to think we're gonna be done soon.

But yeah, I'm kinda sad it's gonna end.

But still excited for all the interviews we have left, too.

[MUSIC] >> I'm getting to the point where I'm like, I miss my family.

And I would like to see my family, but I don't wanna go home.

I think the end is gonna creep up really quickly.

>> At this point, there's so much to learn I'll try my best to get the most out of it.

>> So we're driving, finally, to San Francisco where we end the trip.

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