An interview with

Jobbatical
The Global Future of Work
12 min readSep 22, 2015

Alec Ross

Hillary Clinton’s innovation guru speaks with Jobbatical about immigration, talent mobility, and the future of work.

Alec Ross was a key player in forming the Obama campaign’s tech and innovation strategy in 2008, and served as Hillary Clinton’s Senior Advisor for Innovation. We sat down with Alec in D.C. to hear his thoughts on how gobal connectedness will transform the future of work, and the role he sees Jobbatical playing in it.

You led a charge for national and global innovation during Hillary Clinton’s time as Secretary of State. So tell us, how do you define innovation?

I define innovation two ways. First I define it as the creation of new products or processes that allow for the continuous realization of the future. The second way I define it is Imagination + Commercialization = Innovation. So If you take the commercialization away or if you take the product away from innovation you’ve got imagination, so that’s really the way I think about it. And the difference between imagination and innovation is commercialization. You gotta create a product out of your imagination.

Who do you think is most important in driving innovation forward in a country? Entrepreneurs? Technical creators? Researchers? Consumers? Politicians?

I really think that it’s entrepreneurs. I think that basic research is incredibly important — I think there’s a big gap between basic research and lots of people being able to take advantage of that research. So think about the internet for example. The internet was really created out of a pure research project that began in the late 1960s. The internet existed for effectively 25 years before it commercialized. And it really wasn’t until things like search engines, e-commerce, and things like this came around that took the internet and made it something really widespread. And so it was entrepreneurs, some of whom had an academic background and some of whom didn’t who took the basic research and the creation of the internet, and made it a mass phenomenon.

So I really think that entrepreneurs — while others play important and often indispensable roles, entrepreneurs are the ones who give it scale. What politicians can do is help or hinder innovation. They can create conditions that either accelerate the work of entrepreneurs or f*ck over entrepreneurs. So that’s really it. You know some of the interesting similarities between Estonia and the United States — which is a very rare similarity — is that each country has conditions that are entrepreneur friendly. If you think about how easy it is to pay your taxes in Estonia, or how easy it is to incorporate in Estonia

Definitely. I’m an American e-resident of Estonia, and I could start an Estonian business from here in DC, right now.

Exactly, so that has almost nothing in common with the other European states. When I travel all over Europe people are asking me why the United States is continually the source of innovation, particularly in the digital space, despite the fact that the population size of the EU is larger than the US and despite the fact that there are obviously great engineers all over Europe.

I tell them it comes down to this: public policies in the United States are so much more entrepreneur friendly than the public policies in Europe, with Estonia as a very notable exception.

Let’s talk about a difference though — in Estonia a tiny team like Jobbatical when it first launched can hire someone from almost anywhere in the world, and can get a work permit for them in two days, for less than $100. But in the US it’s so much harder to do that — H1B visas are so difficult and expensive to get.

Yeah, and it’s really so much harder to do that in part because there’s a segment of American society that I think takes a very ugly view of non-Americans, and that has been on full-display now at both Republican presidential debates. Everyone in the United States, all Americans were immigrants at some point, with the exception of the very small number of Native Americans which is less than 1% of the current population. And I think a lot of people, particularly white people whose great grandparents immigrated from countries like Germany and England and Italy have stopped thinking of themselves as the children or grandchildren or great grandchildren of immigrants. They now think of themselves as the “real Americans.” And they are hostile to new waves of immigration.

And so I think that it’s very hard to get these work permits in the United States because there’s this political constituency that fears new waves of immigration and at the heart of that is bigotry and insularity.

“All Americans were immigrants at some point, with the exception of the very small number of Native Americans... And I think a lot of people…now think of themselves as the “real Americans.” And they are hostile to new waves of immigration.“

Right, so today for most Americans, all their coworkers are also American. Do you think that in the increasingly global, connected future that will be a handicap for American businesses?

It will be a handicap. Yes. I think that American businesses will do one of two things: I think that they’re either going to hire more and more internationally, in other countries where labor market conditions are more favorable and the talent exists, or if the US lets those folks into the country then maybe then they’ll hire here in the United states.

Beautiful country, difficult labor policies.

See, where Europe is often its own worst enemy is that while they tend to have more liberal immigration policies they have very difficult labor policies. So part of the reason why economies like France’s and Italy’s have not been as strong as they otherwise might be is that if you’re a CEO you tend not to want to hire people in France or Italy. Because it’s impossible to fire them, because the benefits are so expensive, because there are all of these stipulations attached to employment that are not employer-friendly. And so because these global corporations do not find markets like Italy and France to be indispensable markets, then they’ll hire in other countries that are more labor friendly.

Do you think that this issue is on American politicians’ radars? You’re involved in Hillary Clinton’s current campaign — is it on her radar?

You know I think it’s on a lot of their radars. I think it’s on the radars of the smart politicians and it’s not on the radars of the stupid politicians. I think immigration reform is absolutely at the top of the list for a lot of politicians, both Democrats and Republicans.

But I think that for some of the more chest beating, gorilla-like politicians, they view this issue much more simplistically.

They view it as “Oh we have to protect America and Americans, and only hire people who were born here, whose parents were born here, whose grandparents were born here and who great grandparents were born here.” And their attitudes might resonate with a certain segment with Americans but economically it just doesn’t add up.

It’s pretty ironic that something that is supposedly meant to protect Americans would actually end up handicapping us, business-wise.

Yeah, I mean I grew up in West Virginia, you know I’m a public school kid from West Virginia, there’s not an ounce of blue blood in me. I worked as a midnight janitor when I was in university so you know I come from a sort of working class, middle class background.

Charleston, West Virginia (source here)

And West Virginia is the kind of place that has suffered enormously because of the changing nature of the global economy. And there can be one of two responses to that. One response is “Ok what can we change in order to position ourselves to compete and succeed more effectively?”

Unfortunately that’s the minority response. The majority response is to blame the outside world. And to point fingers and to want to punish others. Rather to make the changes within oneself and within one’s society, to make them increasingly competitive.

And what I hope is that people — you know I wrote this book The Industries of the Future that comes out in February, and I wrote this book not for academics. I could have written it for my social circle of entrepreneurs, and academics and I didn’t. And the reason I didn’t write it for my social circle is that I think there’s already a pretty good understanding in those communities of those challenges. So what I did is I wrote this book trying to reach people who read books, but who are more traditionally middle class, and who wouldn’t normally read about this kind of content.

That sounds great!

I wrote it for them, so that they can start to understand these changes. From AI, machine learning and robotics, to the changing nature of work, to the so-called sharing economy, so that they can start to make some changes themselves.

So what do you think about what we’re doing at Jobbatical in terms of talent mobility and the future of work?

I think it’s incredibly cool. Jobbatical is an indication of what the future of work is going to increasingly look like. It’s no longer going to be the case that you graduate from college, work for a single employer for 30 years, forty hours a week, nine to five, couple weeks of vacation and get a gold watch and a pension. It’s just not the way the world works anymore. Labor is increasingly mobile, it’s increasingly global, it’s increasingly rooted in the individual more than in the employer. It’s increasingly rooted in projects. And so Jobbatical is the right company with the right product at the right time.

“Labor is increasingly mobile, it’s increasingly global, it’s increasingly rooted in the individual more than in the employer. It’s increasingly rooted in projects. And so Jobbatical is the right company with the right product at the right time.”

And also, you know in addition to the macro and micro economic case for Jobbatical, it’s also just kind of fun. You know if you’re suffering through a cold winter in Sweden, then there’s some appeal to maybe spending the months of January, February, March coding in some place that isn’t freezing. So I also think that, in addition to all the economics, I think Jobbatical is also empowering to individuals. I think it gives people choices that they didn’t have before. You know when I was growing up if you said I want to take a sabbatical but I need to work, then your choice was basically to go to Bali or Singapore or some place and be a waiter or a waitress. You couldn’t have gone and done something higher up the labor and wage scale. So what’s really empowering about Jobbatical, is it allows people to make these kinds of changes in their lives. Or to take a diversion in their life in a professionally responsible way. And that’s part of what I find so compelling about it.

Four jobbaticals.

What I also am excited about is that it’s inherently global from day one. I’m excited about how this will allow people to explore parts of the world and test parts of the world that they might otherwise have never explored or tested. So some big destinations now for people might be, say Bali — beautiful place and there might be some risk in going but not a lot. But the way I imagine Jobbatical working in the future, is also having some really frontier opportunities, like the opportunity to work in places in Africa or Central America or South Asia where it might be too big a risk to say I’ll go for a few years, but you’d give anything a chance for a couple months.

Exactly — so for example we recently had an opportunity to do social media in Myanmar.

A gig in Myanmar.

Right — that is just the coolest thing in the world. So I think Jobbatical is just the kind of company that is perfect for this moment in time. And having Karoli running it, as CEO is really compelling too. There’s a couple things that are really compelling — you know I’ve been an entrepreneur and have been working in this field for a long time and there are very few women who are CEOs, and so I like that Karoli who has been in the workforce and who holds patents and who has created things and managed things before is the leader.

I also like that the CEO is coming from Estonia, because I think that it’s increasingly important for people around the world to see that not all of these companies have to be founded and headquartered in an area that is 30 miles long and 15 miles wide called Silicon Valley.

So I think there’s a virtue in that as well. I think that’s great as well — so that’s part of why I’m rooting for Jobbatical.

My final question — if you could take a jobbatical anywhere in the world, let’s say for a year, getting to know a new culture, living and working there, where would you go?

Wow, that sounds great. Ok, so I could argue doing it in a lot of different places. I would probably say for a year maybe South Korea, because it is such an entirely foreign culture that you can’t really understand if you’re there for just a couple days or even a couple weeks. You have to really break through over a sustained period of time to really understand it but at the same time it’s one of the places where the future is being imagined and invented. And if I could spend a year learning Korean, understanding Korean society, Korean innovation, I think that that would be fascinating experience.

Seoul, Korea (source here) — Rabaul, Papua New Guinea (soure here) — Nairobi, Kenya (source here)

Now if the jobbatical were for a shorter period of time, if it were for a month or two then I would do it in some place like Papua New Guinea which I think will grow astronomically in the next ten years but which might not require a year to access and which I might not want to spend a year in. And it if were a halfway point, like six months then I think probably somewhere in East Africa.

Well once your book is out and elections are over, we’ll let you know if we find any gigs for you there!

Bonus: an infographic of ten trends on Alec’s radar that will impact the future of work in the near and distant future. [Coming soon]

Jobbatical exists to connect talented professionals with mind-expanding work experiences in emerging cities around the world. Follow us on Medium for thoughts on the future of work and glimpses of startup life from Bali to Barcelona.

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