>> Only a small fraction of venture capital funding goes to companies founded by women and people of color Which is why three aspiring tech entrepreneurs underrepresented in their field set out on a cross country journey to talk to the trail blazers who came before them.

They hit the road in search of wisdom and guidance to see what it actually takes to turn your idea into a business that impacts the world.

This is Roadtrip Nation: Venture Forward [MUSIC] >> Living and sleeping in the RV isn't as bad as people may think it is.

>> I have no clue where we are.

The RV has been a little tight I think.

I never kinda expected to be in such close quarters with people at all times.

Yeah I really can't get to it [LAUGH].

I feel like we made it more dirty >> I love the people that I'm with this is like another home.

So where are we exactly?

>> Going to Washington DC right now >> I have never been to Washington DC in my life.

We're gonna meet Gary V and Megan Smith all in the same place, Washington DC.

[MUSIC] >> So I felt lost for a while.

Being on this trip, talking to these leaders I'm trying to feel more fine with being confused.

>> I feel like imposter syndrome for me ties more until I have confidence in myself.

How do you grow a company?

How do you invest in people?

How do you invest in yourself?

How do you scale this?

Being a woman in tech, the things I hear are like, about my age, I can't believe you're working on this, shouldn't you be in school right now?

How do you get people to take you seriously.

>> My age is the perfect age for leftover angst from high school plus career anxiety plus you think you know everything now that you're in college and I don't know anything.

And I'm still a kid.

I'm kind of behind I think.

I always feel like I'm behind.

We're interviewing Gary Vanerchuk.

When you think of tech or innovator or entrepreneur, Gary is the usually the first person to come to anyone's mind.

>> Our special guest is Gary Vaynerchuk, the self proclaimed hustler is a digital media mogul.

>> He was the guy who pushed me into marketing.

He was basically my college education.

He just inspires so many people, myself included.

And he got in the earliest stages of the Internet as a wine guy.

>> Hello everyone and welcome to the first episode of Wine Library TV, the first video wine blog.

>> Gary was you can sell wine on the Internet and everyone thought he was crazy but then he just kept evolving and adapting to the changes of the Internet, now he's huge.

>> We didn't just go to his office or something, we went to this speaking arrangement that he was doing.

>> I've been listening to him for past four years online, but it's so crazy to have him say things directly to you.

>> Hi.

>> So just explain everything, we're on a road trip going across the country.

I just graduated college two months ago and I laumched my own marketing agency right after that.

>>Good for you >> Yeah, thanks [LAUGH] [MUSIC] It's so remarkable that we live in a time and age where you could do that.

Nobody a generation older than you would have ever thought to launch their own business.

Just make sure you have it in perspective.

Like if the three of you just said, what is my grandmother doing at this age?

Like when I do that it goes into my parents or stuck in the Soviet Union with no options for anything.

I was born in the Soviet Union Belarus specifically, we came to Queens, New York.

We live in a studio apartment with eight family members.

Super humble beginning.

When I was seven I started really getting into my entrepreneurial gear.

Whatever the weather season, I had a business, right?

Snow, shovel.

The fall, rake leaves.

Summer, wash cars.

So I'm getting D's and F's in school.

Back then, I, by the current standards of success, was a failure.

I would argue, the first 30 years of my life, well first 25 years of my life, everybody on the sidelines was booing me.

That was the best thing that ever happened to me.

Once you embrace adversity and you make it your foundation, it is absolutely the framework of success.

>> I think that I've become more comfortable as the years have gone on with rejection.

>>Good!

>>I think when I decided to become an entrepreneur there was a lot of rejection in that I started selling bracelets and there was just a ton of rejection and that hurt a lot.

>> Dude, honestly, hearing I started selling bracelets like immediately gets me excited.

I mean it.

More than anything, an entrepreneur has to be able to disproportionally deal with rejection.

And I feel like the biggest vulnerability for kids under 25, is that the macro system has been built to not create adversity.

Eighth placed trophies.

>>[LAUGH] That's a way to look at it.

>> It's a very important way to look at it.

Number one thing for an entrepreneur.

You gotta love losing.

>> So a personal question I had is how do I get to that point?

[CROSSTALK] >> I genuinely remember exactly what this felt like.

You want a real pep up?

Go read all the reviews of Crush It, my first book, the negative ones.

Hit that little one star.

Read them all.

I'm a snake oil salesman this internet thing is a fad, social media is stupid.

Nobody is gonna go on Facebook.

Like I'm a big time speaker now.

What nobody talks about is the fact that in 2006 through 2008 I spoke for free all the time at my financial detriment.

And so being underestimated is such a gift and people spend so much time trying to talk themselves out of it.

I would let it fester, put all that push back all those nos, just put it in a little pocket, let it grow.

>> Cool.

>> You see where I'm going?

>>Yeah >> You're not gonna be able to convince them anyway.

I never sell people that are unsellable.

When they don't believe me, I'm like, cool, I'll see you in seven years.

>> [LAUGH] [MUSIC] One thing I'm positive about is [INAUDIBLE].

Look, there's so many things outside of all of us that dictate our lives.

But I feel whether you dwell, or accept outside forces, it doesn't change outside forces.

What's so controllable is you.

You can talk to yourself at 9:30 at night and say, instead of watching this fourth episode of Friends from the 90s on Netflix, maybe I can go do more research.

Maybe I can sell one more bracelet, or maybe learn Java, or Python or.

It just feels controllable.

I like that, I like that.

I worried the people think I'm naive or too ideological about it, I'm not.

I just think it's a motivator and a better framework to put it on yourself, because you can.

What's so controllable is you.

So self awareness is the ultimate drug, you have to figure out who you are.

And if the tune out all the other voices.

All of them.

>> What do you think for someone like me, I wanna find out a way to combine tech and social justice to help my community.

>> Well, that's amazing.

>> [LAUGH] >> The world is your oyster if that's how you think about it.

>> I mean, I don't really see a path in front of me right now, so it's hard to believe that, but.

>> Yeah, the reason I'm excited is if you actually break down your sentence.

And say you wanna use technology or to cross-section technology and to service your community.

When one wants to service their community, whatever that may be, it could be entrepreneurs, it could be immigrants, it could be African-Americans, it could be Asia, it could be anything you want, whatever, right?

Well that's life's work.

You have your whole life to do it.

>> Is this where do I start, right?

>> I think that's right, but I think it's a lot less crippling to think about where you start when you realize you're playing forever.

The great thing that made me fall deeper in love with entrepreneurship was when I realized, oh my god!

I get to play forever.

Not like the athletes that I looked up to.

Not even the, even Jay-Z feels a little old to 15 years olds now, you know what I mean?

And so not a rapper, not an athlete, but an entrepreneur can play forever.

When you have as big of an ambition as what came out of your mouth, if that's your truth.

If it's not young ideology, if it's really in you, then have a lot more patience because special modern medicine, you're probably gonna live 100 more years.

And when you start thinking about I have a 100 years to do this, it gets interesting.

>> [LAUGH] >> What you don't know is that at 42, which seems like 1000 years from now, it feels just like I'm sitting there right now.

If you knew that 42 felt like 20, you would change everything.

It's why I'm trying to get you to understand you have 100 years.

People freak at 18, 22 and 30.

They freak.

They think they have to have it figured out.

It's crazy to have everything figured out at 20.

It's practical and makes more sense to explore 20 to 30, and then double down on something.

That's logical.

And best of all, youngsters, the best thing you've got going for you is you can do everything wrong for the first seven years out of your college and still be a baby.

Literally do everything wrong, and wake up and be 29 and have your whole life in front of you.

[MUSIC] And when you really internalize that, everything changes.

Because right now you got stress on your shoulders that's fake.

You have time, one life, do something.

>> I think that was the first time I ever went speechless in front of someone else, [LAUGH] it's so embarassing.

Thank you so much.

>> You're welcome.

>> [LAUGH] >> Thank you guys.

>> It's just like, we have time to do whatever we want.

>> Like when he said, I still feel like I'm sitting where you are right now.

He kind of said there's no, I know there's no end goal, right, like you said, you're just always learning.

And that is made me feel like I guess I just wanna get started right now and I just need to do something.

>> Exactly.

>> There is time [MUSIC] >> I don't have to have it like right now, it just gonna be like work and progress.

It's worth ultimately, and at the end if you wanna get to a place where you wanna be just put in the hardwork and do like due diligence.

>> I definitely felt the pressure that immigrant parents put on children.

And I still feel that now, and it's really empowering to know if you listen to yourself.

You're gonna get somewhere far, you don't have to listen to your parents.

You don't have to listen to the people around you, this is your life.

>> I think one of the greatest things and many of our leaders have life shown is that ambiguity isn't a bad thing.

That it's okay to not necessarily know where to be, that's all right.

And then I actually feel that I left that interview more sure than when I went in.

[MUSIC] >> You can do this ad then cut like that.

[MUSIC].

>> I feel like this is the college experience, I kind of missed out on.

>> So it's amazing to get out of your normal day to day routine and be exposed to new places and new things.

[MUSIC] >> My eyes are burning feels like there is a fire on my pupils.

>> Take this time and just think about being sad and just get your cry out man [LAUGH].

>> [LAUGH] [MUSIC] >> I've been ruminating about my career path for about a year now.

I just want to integrate my passion for technology and social justice together.

I don't really see a lot of examples of people that have combined the two.

My mom doesn't even know that I'm a minor in Asian American studies, right?

She wouldn't really understand why I'm doing that.

I felt like I was one of the few that really wanted to help my community.

So in that way I always felt alone.

I'm really hoping I can get into talking about tech ethics and maybe working in government to try to figure out how do we use these technologies around us effectively and like make it for all types of people.

That's kind of the people that I want to interview.

People that have made a difference in the world.

[MUSIC] So we get to interview Megan Smith.

[MUSIC] >>Hey, how are you?

>> I'm doing great.

>> Nice to meet you.

>> Who is previous CTO of the White House.

>> The president called and offered me the job, which was incredible.

>> She just had like the most crazy, insane, like most overwhelming resume like I've ever seen in my life.

>> [LAUGH] She was in charge of Business Dev at Google.

>> When I joined Google we were about 1,200 people.

And when I left we were over 50 or 60,000 people.

So it was sort of fly the plane while you're building the plane.

>> She was an engineer working on teams to develop the cutting edge technology that's gonna push society forward.

We called it hypermedia, or multimedia.

Just really beginning of the Internet.

>> Part of general magic who started the whole smartphone thing.

>> We had to start somewhere, we had to start with components that we could buy off the self.

Boxes for that, these are touch screens and there's tons of them.

>> And how small will it finally be big, you think?

>> Someday Dick Tracy wrist watch [LAUGH] >> She's like a visionary, she can see like into the future I feel like >> I'm really an early stage person.

I love to make the new thing >> She's started her own company at shift7 >> Megan's job is to help find people who solving issues and help empower them to do that at a larger scale.

She's been doing this for years like longer than we've been alive.

>> It's just so mind-boggling.

It's crazy to be sitting in front of such a tech legend.

>> You know digital and tech and engineering.

They've been sometimes relegated to this idea that they're for certain robotics or AI or self-driving cars or precision medicine or social media or ad tech stuff.

And it's yes, and any of this stuff is for justice, for education, for health, for people.

Any kind of topic could use any of these subjects, right?

And so I love how you guys are blending things across.

So how can I be helpful?

[MUSIC] >> Your career paths seems to be a lot of exploration, seems very vary, can you talk more about that?

>> It's funny, hen I graduated, go to the career services and you write up your resume.

I had all different things on there but at the bottom, I had the word adventure.

My dad's like that's the number one word.

So I really like to work with incredible people and things that have impact.

My whole career has been following my intuition and having incredible advice from people around.

And so I found when I was younger, meeting people who were doing jobs or things that I was interested or something like it was really helpful because it made it a lot more tangible.

And finding people who look like you helped too, because another biggest challenges is in tech is that it's gone way off the charts accelerating certain people and just diminishing others.

That kind of Mark Zuckerberg looking person, Jeff Bezos looking person, we love them, but they're not the only people.

And it's one of the greatest challenges in our country.

>> And so it's just like kind of going off of that.

But how would you go about empowering minorities or under represented people that like they don't even know where to start really?

How do they go about launching their own thing?

>> Right, I always study history, I do it because there's an incredible of quote that Churchill says, the further back you can look the further forward you will see.

History has been told in a really imbalanced way.

And so you have to dig a little more.

So for example, we talk a little bit about, say justice technologies, or helping each other technologies.

If you don't know about Jane Adams, I don't know if you guys have ever heard of this person, have you?

Probably not, yeah.

Three children died in Chicago because their parents were at work.

Industrial age in Chicago think of the crazy work conditions, and pollution and everything.

She knew about settlement houses from England and she and her friend they built something called Hull House.

They moved right into the poorest neighborhoods, and she develops basically what becomes social work.

And she wins the Nobel peace prize for inventing social work.

And yet you've never heard of her.

This is an Edison level American, Ida B.

Wells, she was born six months before the Emancipation Proclamation.

So at New Year's under six month old moment she became free, and she went on to become one of the greatest civil rights leaders ever.

And one of the greatest American data scientists in the history of our country.

Grace Hopper, she invented computer languages.

She said, what if we could code in a human language, we could broaden participation.

And everybody said no one wants to do that.

And one of the greatest pieces of advice I heard that she'd said was don't let them tell you you're wrong if you're not.

From a design perspective Susan Care did all the graphic design.

If I look at my phone like that, all of these icons, she did emojis.

This is like 1992.

She did all the graphics for the Mac.

That then, Windows was using, that then became our phones, that went everywhere.

So she's probably one of the people in the world who has the most influence on all of us, because it's the interface and the visuals and that's very much Susan's innovation.

So when you're doing this work, it's important to know about the history of these people.

I love that you are doing Asian America's studies.

That's incredible.

It's so powerful.

And you are gonna discover people who are just looking at WASP's, the women who were the air service pilots, and women like Maggie Gee.

And others that we just have them now about the extraordinary work that they did.

So knowing about these heroes, I think we'll help you guys know that you belong.

We're in the beautiful room here at the National Academy of Science and in this building of course we know science and technology were little biased towards one section.

So you see England, so that's Egypt, Rome.

You see only those ones are celebrated.

One of my goals is we would have all the different continents, and slowly expand as we know that everybody's doing amazing things the whole time.

You guys are part of a continuum of all these people for the whole history of our country.

Who even though it's maybe not written properly in the history books, who look like everybody the whole time.

We all have in part of inventing and creating the country including science and technology, be confident and that we belong in these fields, >> I am just doing computer science and Asian American Studies are now the concrete paths in front of me are PM, software engineering, none of these seem to lead to the government.

So I don't really know what I should do next.

Is there a concrete path to the government?

>> What's interesting about government is, it's touching every part of our lives.

So any topic you're interested in, there's gonna be someplace in government that you could do.

The government's just us.

It's like whoever shows up will be the government, and who ever doesn't that's the loss.

And so when I'm excited about you guys having technical backgrounds you can bring those skills into these wonderful yet a little bit dusty and bureaucratic spaces, right?

It's not like this is a new start up, the States of Americas, it is couple of hundred years old and everybody makes their mark.

And that would be a great way to come into government.

And then find people like me and I'd be happy to riff with you on the area thing.

We're out here and we'd love to have you guys join us.

We all come with different histories.

And we all have to notice that those histories are culture add.

This is weird idea Silicon Valley had of culture fit is very destructive.

I don't want you to fit.

I want you to add.

And so what you guys are doing together is you're helping show that everybody belongs in entrepreneurship.

Gives you great hope.

[MUSIC] >> She's everything.

>> She's a medical fairy that just helps everybody.

>> She's very empowering,I feel so much more empowered.

>> She's been able to have such a varied career and it's all because of her intuition.

I guess I should start listening- >> [LAUGH] >> To myself more, I don't know.

I just, wow.

People tell you things, and your'e supposed to do this and that and whatever, and you're like, okay, this is what I have to do to be successful or something.

And this road trip is just, I'm throwing all that out the window.

I'm just gonna do what I want.

[LAUGH] That's how I need to structure my life.

I should just think about what I wanna do, this isn't about money, this isn't about going to big tech company, my original goal is to help people.

And I can still pursue that.

>> Yeah at Megan Smith interview was amazing.

It's just like something I aspire to be like.

All the work that she's done is just incredible.

>> It was very empowering.

She's working on these exciting technologies, and I kind of see myself in a role similar to hers.

I think she was incredibly validating on beliefs and following passions and things that you care about.

>> I have a lot of voices in my houses telling me I should do this or that.

This is a really good thing for me being able to take time off my regular day to day thoughts.

Just seeing all these leaders, humble themselves and be like, I don't know what I was doing, but I'm a CTO of the US.

I'm confused, and I might be president one day.

[LAUGH] It's okay.

[MUSIC] So the next interview is coming up.

I hope they can follow up with the ones that we've had so far cuz the four we had already we're so great.

But I'm still just as excited to meet the next people.

[MUSIC] >> I feel like talking to more people and connecting to them on a deeper level, I'm learning more about myself.

>> The experiences that I'm having on the trip are giving me a moment to reflect and think about myself in a new context.

I'm excited.

[MUSIC] >>We're more than halfway through the trip >> I've never been to Detroit before.

>> My purpose was to come over here to transform the block.

>> She's just an amazing person.

>> There's not enough women in tech.

There's not enough people of color.

You guys are the future.

>> One percent of venture funding goes to African Americans.

I used to contemplate, do I need to hire a white guy to be the face, and I'd just be the idea.

The clear answer was, I can do this myself.

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

[MUSIC]