I first met CNBC’s Julia Boorstin during my days at YouTube. As CNBC’s Senior Media & Entertainment Correspondent she had a really sharp POV on how we were evolving as a platform. Additionally when she heard about the work I was doing with YouTube as a platform for causes and non-profits, she immediately offered to introduce me to several Hollywood executives who had shared goals. Since she was at the Oscars last night, this seemed like a great day to publish our recent chat.

Hunter Walk: Your reporting career began as a writer but you relatively quickly added an on-camera role with CNBC. Was being “on-stage” an easy transition for you – are there photos of young Julia starring in her high school production of Cats? Or was there a different motivation for the switch?

Julia Boorstin: Well, I never did CATS—I have a terrible singing voice—but I did do the Nutcracker, and various other dance performances and plenty of high school speech and debate. I started dancing when I was four, and I was pretty serious about ballet and danced in a professional Nutcracker before moving on to modern dance, which I continued with through college.

That said, I didn’t start at Fortune Magazine out of college with any expectation of being a journalist on-camera. I was nudged into it by my former boss and amazing mentor Andy Serwer who was overloaded with a ton of TV requests. Fortune and CNN had a partnership; I first appeared to talk about an article I’d written in 2001 about the bubble bursting. When it turned out I didn’t freeze and was comfortable bantering with the anchors, it morphed into a regular thing, with segments a couple times a week on CNN Headline News.

I remember when I first interviewed with CNBC chief Mark Hoffman about a decade ago. he asked if I had any experience on stage. When I explained that I had danced, he said if I could be on stage in a leotard, with the risk of falling on my face in front of hundreds of people, then being on TV in a blazer would be no problem. He was right!

HW: This year you’ll celebrate 10 years at CNBC. That’s been the period of time where we’ve also seen social platforms such as Facebook, Twitter and YouTube emerge. How have these products become part of your toolbox? Are you active on Snapchat yet – either personally or with CNBC content?

JB: I can’t believe it—it’s flown by! It’s been such a thrill to cover these game-changing products from their infancy. I use Twitter as my newsfeed—it’s one of the first things I check in the morning and I have Tweetdeck up throughout the day. I also Tweet about upcoming interviews and clips and articles I’ve written on CNBC.com. I’m also a big retweeter.

I post my Tweets to my public Facebook profile, but am looking to do more there—especially with the new live video feature. I am on Facebook a lot – definitely a DAU (daily active user), but I’m on my personal profile. I’m amazed how Messenger has allowed me to easily connect with so many old friends, and I find it invaluable —  to keep in touch with far-flung classmates and connect with old friends.

Interestingly, recently I’ve been spending a lot more time on Facebook, because I’ve been reading a ton of articles I’ve come across there. (The ‘Instant Articles’ feature is definitely working on me. I’m a LinkedIn Influencer, but really should be posting more there. And while CNBC is active on Snapchat, I’m not doing much. I’m hopeful that CNBC will be included in Snapchat’s Discover feature, and I’ve been talking to CNBC’s growing social team about doing more on the platform.

It’s amazing how all these new platforms have sped up the pace of journalism and everything else. When I started at Fortune Magazine I would have weeks- and occasionally months—to report and write a story. In TV it was typical to have a day to write and put together a package. But as I started doing more breaking news and Twitter (and everything else) sped up the pace of news, I often have to tweet instant analysis or quickly write up 500 words for CNBC.com.

HW: Often your coverage spans tech and media, two worlds that historically have accused the other of just not “getting it” – the gap between LA and Silicon Valley. Was that trope ever truly true? Has it changed in recent years? Do you foresee advances such as Virtual Reality dependent upon engineers and creatives collaborating?

JB: Media and Internet companies – Hollywood and Silicon Valley—are more interconnected now than ever. And they’re only going to become even more intertwined. Many of the Internet giants – which we think of as ‘tech companies’ are next-generation media companies. Look at Netflix and most recently Apple going beyond just distributing content to make their own. And ad-giants Facebook and YouTube are competing with newspapers – and every other type of content—for consumers attention and ad dollars. And on the other end, CNBC’s parent company Comcast, defines itself as a technology company. Just look at the most recent earnings season—the focus has been entirely on how media giants are using technology to adapt to the digital future.

I don’t think that the two types of companies didn’t, or don’t *get* each other. They see that they take different approaches to content; they have a different sense of the value of pure creativity or “art” versus a data-driven approach. They know they need each other. And these days it’s not uncommon to see tech titans at Oscar and Golden Globes parties. Sometimes they look out of place, but they’ve definitely have a place there.

But yes, fundamentally, technology, and creative arts have always interacted with some friction. Think back to Edison: he invented the Kinetograph camera and the Kinetoscope projector. But then he sued filmmakers who used similar technology. The legal battles between tech-oriented distributors and content creators has certainly continued—think Viacom suing YouTube and ESPN suing Verizon over its skinny bundle. Content and distribution—Hollywood and Silicon Valley—they just have different ideas of what’s most valuable.

HW: What’s one company, person or topic you wish audiences cared more about? And why do you think it’s been a tough one to cover?

JB: This is a tough one to answer. It’s always disappointing when enterprise stories I’ve been working on get killed for breaking news, but I definitely understand those decisions, especially with the market as volatile as it’s been. I think one general area I wish we could do more on is philanthropy—I think it’s fascinating to watch how some of the most astute, disruptive business practices of our generation are being applied to non-profit models. I think it’s an area of interest for CNBC viewers, but as it’s not viewed as part of the market-driven forces of our economy or viewed as key to our focus on actionable news, I think it’s hard to give it as much attention as it deserves.

HW: You’re a tv pro. Any tips for folks who find themselves on live tv? I was always told to not gesture as wildly as I might in person because it appears exaggerated on-screen.

JB: Relax, smile, and look straight into the camera (or directly at the person interviewing you, depending on the format). I find the most awkward looking interviews are when people are alone in a studio, don’t know where to look, and end up squirming. I find when I get nervous I talk too quickly and my voice raises by about an octave. Oh, and don’t wear stripes or houndstooth. The more you can relax, the better! Remember that they asked you on for a reason, so there’s no reason to be worried!

The TechCrunch to Venture Capital path is well-understood, but TechCrunch to business school? Not quite yet the same trope. Alexia Tsotsis stepped away from her co-EIC role at TechCrunch last year to enroll in the Sloan program at Stanford – essentially a one year MBA. 

Hunter Walk: So I know a bit about the Stanford Biz School Sloan Program you’re currently doing since my wife graduated from it too. What was your motivation? Had you been thinking about grad school for a while?

Alexia Tsotsis: If you stop learning, you stop living. I’ve always wanted to go to business school, ever since I knew what it was, and I’ve always wanted to go to Stanford. I went back to school specifically when I did because I was hungry to learn the financial mechanics (the return modeling, etc) behind the startups I had been covering as a writer, in order to better understand them as an analyst and investor. And, I really missed math.

HW: You most recently were co-Editor In Chief of TechCrunch, which put you in a bit in the maelstrom of TC’s own transformation as part of AOL and shifting from reporting to managing. With some additional perspective now having stepped away, how would you describe your period of leadership? What are you most proud of? What might you have done differently?

AT: I owe a lot to Michael Arrington (who hired me), Eric Eldon (who promoted me) and to Matthew Panzarino, who served as co-editor with me. I’m most proud of TechCrunch’s efforts to highlight diversity in tech during and after my time — our $50k Include Diversity program was founded during Eldon and I’s tenure. Both Eric and I and Matthew and I tried to emphasize having a point of view and taking a stand as writers — I wouldn’t do anything differently, but would double down on this point if I were somehow given a do-over.

HW: Are there reporters (covering tech or otherwise) who you just think “damn, they’re an awesome writer!!!” Who do you admire and why?

AT: The aforementioned three in addition to Om Malik, Kara Swisher, Casey Newton, Nitasha Tiku, John Gruber and Kim-Mai Cutler, because they all have a unique voice. I’m addicted to Dan Primack’s daily newsletter, and am glad my former colleague Leena Rao joined him at Fortune. In the same vein, I think my former colleague Colleen Taylor is doing a solid job editing The Macro, and I regularly peruse the work of a lot of the writers I used to work with at TC.

As for non-reporters, I enjoy reading Chris Dixon, Paul Graham, Fred Wilson, Sarah Tavel, Ben Horowitz, MG Siegler, Sam Altman, Joelle Emerson, Hunter Walk [hw note: aww thanks!], Tracy Chou and Mark Suster as well as many others. I also still read Techmeme as much as I did when I was TC co-editor.

HW: Are female journalists (and editors) judged differently than their male counterparts? Were there ever times – maybe when you were doing an interview, or discussing a topic you wanted to cover – where you felt like gender started to factor in?

AT: I’m going to reframe the question: Should gender factor in to any work you do? Unequivocally no. I think we’re heading towards a world where it won’t, and will do as much as I can to make sure that future gets here faster.

HW: What company/topic do you think gets too much attention from today’s tech reporters? What company/topic not enough?

AT: Too much attention: Apple, Facebook, Google and teenage “Snapchats per minute.” Not enough: Privacy, ed-tech, health-tech and other innovations that can help materially improve life, both here and in the developing world.

Elle Luna and I met several years ago via overlapping friend circles. The last meal we shared, several years ago, she departed accepting a ride in a pedicab piloted by a man in a spiderman costume. That kinda summarizes how wonderful her journey of the past several years have been.

Hunter Walk: Your book, The Crossroads of Should and Must, has really reverberated with the creative community. Did you originally write it for yourself or for others? Did it feel like a risk opening yourself up in that way?

Elle Luna: I got to a place in my life where I was asking a lot of questions. While I didn’t have the answers, I wasn’t really sure if I needed to because the questions in and of themselves were valuable. I wanted to understand what kind of work I was doing and why. Did I have a job, a career, or a calling? I wanted to know what my passion was, find my personal myth, and still keep a roof over my head. So I collected these questions, hit “publish” on an essay and within two weeks, it was shared to over five million people on Twitter. It turned out that a lot of people were asking similar questions. The blog post became a book and here we are.

Prior to publishing the blog post, I had been working at Mailbox, launching our iPhone app. I was the design lead and our mission was to revolutionize email for the mobile phone. Our launch was an unmitigated success, and I recall the deep joy and gratitude I felt about being a part of this team that built a tool that we felt would lighten the loads of people who were burdened by email. While things were going really well with our product launch, I was exhausted. Really, really exhausted.

I needed a rest, a retreat. Not just for a weekend or a week, but I needed to step away from it all. What I wanted was more than just a literal rest, but also a restful mind—free from all of the busyness of life, free from all of the hecticness that comes from goal-orientedness and meetings meetings meetings and all of the trappings of the corporate world. Which, admittedly, I adored, but I realized was causing a lot of trappings for me in my life.

Aristotle has a great name for this, he called it the tabula rasa. It means blank slate. I needed a tabula rasa where I could go and hear myself think, free from all of the external voices telling me how I should and shouldn’t live my life.

This was the moment that the crossroads appeared very clearly in my life: Should or Must? I was looking down two roads, and they were both appealing in their own ways, but they were different, and I had to choose. I reviewed my finances and saw that I could buy myself a window of time to step away from my job. In true blank slate form, I did not know what the future held, but I knew that I needed to leave, and so I put in my notice and quit.

I went home to my tabula rasa, a studio space in San Francisco, and my journey with art began to unfold. Along the way, I started to accumulate these questions, and once these ideas grew larger and more solidified, I shared them.

I’ve come to realize that the reason the post spoke to so many people is because we all arrive at this crossroads between Should and Must over and over again throughout our lives. Sometimes it’s a really big crossroads, and other times, it’s smaller. But we are constantly faced with the same question, again and again, and it is this— obey Should or honor Must?

HW: I’m sure you’ve gotten a ton of notes from people saying how Crossroads helped them take a new step in their lives. Any consistent fears in what was holding people back?

EL: The most common question I get is this one: “What if doing what I love doesn’t pay?” It’s a great question. I once watched this TED talk by Stefan Sagmeister that just blew me away. He talked about the differences between Jobs, Careers, and Callings. Jobs are activities we typically do from 9-5, for pay; Careers are systems of advancements over time where rewards are used to optimize behavior; and Callings are activities, or hobbies, even, which are pursued for intrinsic value, either with or without pay. This really caught me because I had never thought about the different modes of work. Have you? It made me wonder what I had… a job? a career? a calling? Or perhaps some mix of the three. It turns out that really wise people throughout time have combined these activities in different ways, which was inspiring. TS Elliot, for example, had a calling to be an author, which is why we know about him today. But did you know that he was also a banker? He was a brilliant financial mind in London. And I imagine that having a career as a banker created the space for him to pursue his passion. Similarly, I recently heard Elizabeth Gilbert give a talk where she said that she told her art that she would never, ever ask for it to put a roof over her head. She worked odd jobs until, one day, her books began making money and putting a roof over her head. It’s a good question to ask our callings: “Hey calling! Do you want to be responsible for paying the rent?” You might have a job 9-5 while you pursue your calling on nights and weekends. Or, you might pursue your calling 24/7 and make a living from it. There’s no right answer. And there’s dignity in all work. Just because you do something for money doesn’t make it dirty. You get to decide what’s right for you and your life.

While we place the blame on money, time or space as reasons for not pursuing our Must, I think the real reason we don’t go for it is something else. Something scarier. Something spoken about a lot less.

Should.

Should is how other people want us to live our lives. It’s all of the expectations and obligations that others layer upon us. Sometimes Shoulds are small, like “You should check out this movie!” Other times, Shoulds are large and insidious, like “You should sit in the back of the bus because of your skin color” or “You should not be educated because you are a girl.” When we choose Should, we can feel it in our bodies. Our muscles constrict, our body tenses. It’s an awful feeling. And the part that’s really hard is when culture at large says that we Should do something that we deeply, inwardly know is really wrong for us. When we live our lives in Should, we are essentially choosing to live our life for someone or something other than ourselves.

And the reason Should is so tricky is because Shoulds are put on us from the moment we’re born. This is an evolutionary process because we are essentially born wild creatures. Ask anyone with a toddler, they know! And parents place Shoulds on their children so that those wild creatures will know how to survive in this world. This is the process of socialization, and that’s what Shoulds do, they teach us how to survive.

Now, as the child grows up, it is a healthy process for them to examine those Shoulds, to question them, and to shed the Shoulds that do not serve their unique, evolving truth as a person. These are the Shoulds placed on them by family, community, and culture at large. This is the process of individuation, and it is very important. But sometimes, this process is delayed, or, at worst, doesn’t happen at all. We might even find ourselves as adults still living in a world of Shoulds from childhood that we inherited but never consciously examined.

When I talk about the process of shedding Shoulds, there seems to be a shift, a very palpable shift. Just this past week, I spoke at ALT Summit in Salt Lake City, and as I talked about how to bring our Shoulds into consciousness, I could feel the energy in the room relax, or was it release? As though suddenly there was a way to move forward, a way to bring those outdated belief systems to the surface and bring love to what had previously been hidden or shamed into not being seen or heard.

Where I’m headed now with my work is uncovering more about what Shoulds are like as a woman. Now, whether you’re a woman, a man, Latino, African American… are there Shoulds keep you categorized as that? Shoulds that keep you imprisoned? As I bring my Shoulds into consciousness, I’m asking: what Shoulds do I feel that society holds me accountable for? What are women obligated to do? This process has been a tremendously beautiful one, and in the book, I share a few methods that you can use to examine your  own Shoulds. But the reason this works, the reason it brings so much liberation to our lives is because Should is the doorkeeper to Must, the counterforce that works against even our very best intentions. So long as Should has a grip on us, our Must doesn’t stand a chance! And if our Must is strong and powerful without having dealt with Should, just wait until you’re really set loose! It’s like that great Janis Joplin lyric, “Freedom’s just another word for nothing left to lose.”

If we want to be free, we first have to understand why we are not free, what keeps us from being free. As we bring Shoulds into consciousness, they loosen their grip on our lives. That which was previously painful and avoided is now understood and served. That which once roused fear and anxiety is now transformed and inspires compassion. To bring our Shoulds into view is a miraculous gift, not only because your load lightens and your spirit becomes brighter, but also to know that your superpowers, your truest, deepest, most unique gifts, the light that you have been carrying and nurturing your whole life, is now ready to come forth and shine, shine, shine. If I have learned one thing from this journey, it’s that choosing Must, honoring who we are and why we are here, is the greatest thing we can do with our lives.

HW: From your Instagram feed, I see you doing a lot of international travel. Have you found differences across cultures in what it means to be creative?

EL: I recently had the tremendous privilege of being around some seriously brave, radiant and courageous people. I was at a girl’s school in rural Uttar Pradesh, India, which is the base of the base of the base of the pyramid. Here, where having a toilet is a luxury and being able to properly nourish your family and animals is practically impossible, there is a haven, a utopia for girls to get an education, which is equally unthinkable in a place where child marriages are all too common and the thought of educating a girl child simply doesn’t make economic sense to a frightening number of families. This school, called Pardada Pardadi, provides education, meals, doctors, education on rights, computer access… you name it… to girls pre-K through 12th grade. The founder, an incredible man named Sam Singh, decided to return to his hometown village and build this school after making what he calls “a dollar” as an SVP at DuPont. He chose to use his success to uplift his childhood community. It was his Must, even as people doubted his vision. It was his Must, even as angry disbelievers showered his car with bullets in Delhi (he was unhurt). It was his Must as four girls turned into fourteen hundred. Sam’s advice for anyone trying to make change is to just keep moving forward, to just keep going, to not stop, no matter what.

Just a few weeks ago, Sam Sing was on the “Jimmy Fallon Show” of India being interviewed about this incredible school that is changing the paradigm for girls. A school that was at first such a threat to the status quo is now being heralded as the future for education in India! Amazing, right? And to think, it all started because Sam believed, unwaveringly, in his Must. It makes me wonder if our journeys within don’t ultimately guide us back to our communities, a place to use our passions and talents to serve one another?

HW: From your experience as an author, what does the publishing industry feel like? How did it compare to your work as a designer in tech?

EL: Well, I suppose there are obvious differences. You can’t fix a bug in a printed artifact and you can’t push an update if something isn’t clear. A book is a snapshot of time, it’s of a moment, mistakes and all. Luckily, I haven’t caught a mistake, and I haven’t wanted to push any updates, but it definitely gave me serious pause before hitting “print.” I couldn’t shake the thought that if I had kids one day, they’d find this object in their library. Isn’t that funny? That was one of my biggest concerns: is what I’m about to say going to help our littlest people to live more joyful, peaceful, fulfilling lives?

A similarity between publishing and tech is that both have this incredible opportunity to create vehicles for ideas that help people. This begs the question, what happens when the vehicle is gone? For example, like anyone else who launched Mailbox today, I saw the sad message that it will be shutting down in a few days. Does this mean Mailbox is gone? Of course not. We have all of the lessons learned. We have the beauty of the dance between our design and engineering teams. We have the experiential elements that enabled an interaction that, in my own opinion, was magical. I see Mailbox everywhere—in other products, in how teams are being built, and in company culture. I suppose this is sort of a Buddhist idea, that things never really die—that there is an inter-being amongst all things. I believe in that. The same thing is true for the book. Once you plant a seed in someone’s head about Should and Must, once they begin to wonder if they’re living their life for someone or something other than themselves, once they begin that miraculous inward journey of reconnecting with their own voice, their own beliefs, and their own most authentic self, their heart is changed and you can see it. Their actions change. The person is evolving. It is unspeakably beautiful to experience someone seeking their personal truth, their personal myth. As Thoreau once said, “Convince me that you have a seed there, and I am prepared to expect miracles.”

HW: Any more books in you?

EL: Yes! I am finishing the art for my dear friend’s memoir. Keep your eyes peeled! In the meantime, you can check out The Crossroads of Should and Must here.

My business is about investing in extraordinary founder talent so it pains me that I can’t write a Homebrew Term Sheet to Laura Weidman Powers. But alas, she’s changing the world through another awesome channel right now, CODE2040. I’ve gotten to know CODE2040 as a Mentor, Panelist and Donor. And here I get to know her a little better via Five Questions:

Hunter Walk: We met during CODE2040’s first class of students. I was at YouTube and fortunate enough to be a CODE2040 Mentor that summer. Can you share how the organization got started and what the year “2040” refers to?

Laura Weidman Powers: Tristan Walker and I started CODE2040 after working in tech and recognizing 1) how much opportunity there is in this space but 2) how little diversity there is – this was particularly true when we started the organization in early 2012. We chose the name CODE2040 as a call to action: the year 2040 is the year that people of color will be the majority in the United States, and we want to see a tech industry that reflects the country by that time.

No one was really talking about diversity in tech in 2012 and there wasn’t much happening by way of solving the problem so we decided to just jump in and pilot and learn. We launched the CODE2040 Fellows Program, which places top black and Latino/a software engineering students in internships, with five students in summer 2012. This year, in 2016, we will have about 60 Fellows – and we run three other programs for students, entrepreneurs, and tech companies, as well, reaching about 1,000 people a year across all programs.

HW: You’ve been very deliberate in expanding CODE2040 program size over time – not wanting to move too quickly in the early years. What foundation did you seek to put in place and how do you decide if you’re ready to grow?

LWP: We were really deliberate in our growth. For the first three years, CODE2040 was synonymous with the CODE2040 Fellows Program. It is our flagship. We had five students, then 18, then 25. Throughout that time we weren’t just running and growing the program, we were learning. We knew people wanted us to do more – students, companies – but we wanted to make sure that we weren’t just throwing darts, but rather that we were leveraging existing knowledge to run smart experiments.

In 2014 we felt like we’d learned enough about what additional supports college students needed to prep for tech’s idiosyncratic interview processes that we could start piloting some new programming. That lead to TAP (Technical Applicant Prep Program), the pilot of which was funded by Google.org. We partnered with Google for Entrepreneurs in 2015 to begin to bring our work national, with a focus on entrepreneurial ecosystems.

This has always been core to what we care about – increasing representation for blacks and Latino/as in tech – and in the Valley it took the form of the Fellows Program. TAP extended our student-focused work. As we go into other markets, we can choose whether it makes sense to be more student-oriented or ecosystem-oriented with the CODE2040 Residency.

And now, in 2016, we’re growing our programming for companies. We found that the companies we were working with (about 70 partners to date, 42 this year) want talent, yes, but they also want process improvements, culture shifts, coaching – so we’re building out programming that is just for company partners to empower them to create their own change internally.

HW: How do you structure CODE2040’s funding base? Is there a revenue generating aspect to the organization that makes it self-sustainable?

LWP: One of my main goals for CODE2040 is for it to be self-sustaining from a revenue perspective. We are addressing a market failure with CODE2040, and so philanthropic capital is completely necessary at this moment in time. However, earned revenue is great too because it gives us security as well as freedom to experiment, learn, fail, and ultimately succeed.

The Fellows Program is a great example of an earned revenue strategy that’s gone well. It took four years, but the revenue we get from company partners participating in the Fellows Program just about covers program costs – we expect to be able to cover Fellows Program costs, allocated overhead, and begin to support the development of new resources for company partners starting this year.

The CODE2040 Residency is an example of another funding model that works well. It’s a program partnership with Google for Entrepreneurs. We work closely with the GFE and Google Ventures teams on design, development, and implementation, and they underwrite the program in exchange for us implementing it with their partners.

Our other programs like TAP are newer, so they still have a ways to go until they are self-sufficient – they require philanthropic capital. We think of that money as an investment – like seed funding or a Series A. It’s necessary to get a program on its feet and to provide a runway to develop an earned revenue model down the line – sometimes that takes time.

In addition to launching and sustaining newer programs, philanthropic capital is vital to CODE2040’s growth as an organization. Even when a program like the Fellows Program can cover its own costs, we still need to be able to invest in the growth and sustainability of the organization as a whole. We’re hiring a lot right now – we brought on a COO in the fall, we’re hiring for more program staff and a director of talent now. These are investments that may require philanthropic capital to start, but that we can then factor into our revenue models.

HW: When you track the process of CODE2040’s Fellows post-program and post-graduation, what trends are you starting to see? How do you think about efficacy and ROI?

LWP: We’re so excited by what we’re seeing with our alums. This past summer, 90% of our Fellows received return offers from their summer employers – a really strong vote of confidence in our partner companies’ believe that these are talented developers that belong in the Valley full time. For the first time this past summer we had a CODE2040 alum working at a partner company who was managing the partner’s CODE2040 summer interns!

We also see some of our Fellows starting their own companies. One of our first five runs a company called Wise Systems. They just went through Techstars in Boston. We have another group of Fellows in Y Combinator’s fellowship program with Shypmate. It’s been so thrilling to see what our Fellows have done and continue to do!

HW: Are you tired of hearing people talk about diversity? Do we talk too much with not enough action and accountability, or is the increased visibility of the problem an important foundational step?

LWP: I definitely don’t think we talk about diversity too much. It’s such a hard topic for people to get comfortable with that I think the more it’s on the tips of our lips the better. That said, talk does not replace action, of course. And if talk is all we’re doing, we’ll never see progress.

I see all the talk as opening the door. When tech companies started releasing their diversity data in Spring 2014 that not only changed the conversation, it changed the actions companies took. Transparency breeds accountability in this case, I think.

Now companies need to be willing to experience and change. Some really are – I’ve started to hear more and more companies talk about shifting policies, practices, culture – that’s really exciting. So I’m optimistic. Change is hard and change is slow. But I think we’re on the right track.

While leading product at YouTube I fell in love with the Next New Networks team, one of the first startups to understand how to build content for YouTube and assist networks of creators. For a variety of blah blah big company reasons, I failed in my first attempt to acquire them. Thankfully, we tried again and the NNN team came over to YouTube in 2011. Vanessa Pappas immediately made an impact upon the way YouTube approached audience development. Five years later, here are five questions for this sharp Australian turned New Yorker.

Hunter Walk: So you joined YouTube in 2011 when Next New Networks was acquired. You were quite familiar with YouTube because you worked closely with many content creators and some of YouTube’s teams. Do you remember your first impressions when you came aboard – were there things which surprised you about YouTube, that weren’t apparent when you were on the outside?

Vanessa Pappas: Yes! There were a couple things that really stood out to me when I joined. First the idea that anyone could bring an idea to the table, that even though YouTube was a big company, sitting inside an even bigger company, that there was a true openness and appetite for experimentation. Coming from a startup environment the mentalities were similar, YouTube didn’t presume to have all the answers and that was really reassuring. We were given the opportunity to try things. Whether it was when I lead the launch of our Creator Playbook for YouTube best practices worldwide or when we opened our first YouTube Space, there was a test and iterate mode that we could operate within.

Second was just the sheer scale of the platform. At Next New, we worked with a little more than a hundred creators but that was nowhere near the millions of creators who are on YouTube and its billion users, not to mention the data that we instantly had access to. I think you hear the numbers when you’re on the outside but it doesn’t really resonate in the same way until you are actually doing something that has the potential to impact millions, globally. It’s truly motivating, but also a little humbling in the responsibility that comes with it.

HW: YouTube, for me, was always product that required both algorithms AND anthropology to thrive. That is, the team couldn’t be only data driven but had to understand communities, creativity and people. As Global Head of Creative Insights at YouTube are there times that the data says one thing but your instincts suggest something else? And what do you trust?

VP: YouTube is such a unique platform in that regard. I think YouTube communities are unparalleled, in terms of both their passion and engagement and the breadth of our communities and the content. In my role, it’s my job to understand what works to build an audience on YouTube from a creative and data-driven perspective. And while it’s certainly easy to look at the numbers and make assumptions about what resonates with users, you really do need to pair that with your instincts and importantly, trust the creators’ instincts. More often it requires you to look beneath the surface. Typically what I find is the data will tell you a macro trend that you’re witnessing (e.g. whether a feature or a content format type is successful) but as you look deeper you recognize that it plays out differently for subsets of the viewer base and by market. And knowing to dig further comes from trusting your gut.

That said, I also feel you need to question your own assumptions and biases. In a landscape where things change so rapidly some things that were true yesterday may not be true today. The platform is constantly evolving and with that, new behaviors arise. For example we’ve been AB testing a feature that’s been out for a while, and a year ago it gave one set of results and now we’re seeing that the opposite can be true in terms of how viewers respond. So I really believe it’s a matter of maintaining an inquisitiveness and flexing both left and right sides of the brain.

HW: Historically there’s been a language and credibility gap separating Silicon Valley and Hollywood. Is this gap widening, narrowing or who cares because the future will look totally different?

VP: It is rapidly narrowing. It wasn’t too long ago that Variety thought we we’re all doomed if PewDiePie was an example of talent, to now recognizing YouTubers are more popular than mainstream celebrities. So, while it’s felt a long time coming for those who’ve been on the digital side I think we’re starting to see Hollywood come around as the audience shift has been so undeniable and there are no signs of it stopping. The next few years the landscape is going to be radically different again with the next technological advances with The Internet of Things, VR and 360 gaining their foothold.

HW: How has YouTube’s Creator population changed over the last few years? Do you see any common threads running through the generations?

VP: I think the biggest changes are the massive growth in terms of numbers in our creator community. And with that, the breadth and depth of content – there’s literally an audience for everything. Outside of more common communities that exist on YouTube around music, film, gaming, hobbies, tutorials, animation, makeup and so on we’ve found niche communities around everything from haul videos, to drone racing, to miniature things, to parkour. It wasn’t too long ago that Minecraft videos and toy unboxing were anything but mainstream.

Next I’d say is the maturity of our creators. This isn’t just vloggers in their bedroom. Our creators are running full-fledged production companies and businesses where they’re franchising into books, TV shows, movies and products. For example, Michelle Phan, Tyler Oakley, Grace Helbig, Bethany Mota, and Rooster Teeth. And what’s great to see is the audience has really come along for the ride.

In terms of commonalities that we see today with past generations, and this may sound trite, but the authenticity of the content is still one of the main distinguishing factors on why YouTube creators resonate so deeply with audiences. That, and the fact that consistency of programming works. At the end of the day, humans are habitual creatures so certainly what works on TV, in terms of reliable programming, is also true of online. I think one the biggest changes has been this shift to regular scheduled programming for online creators. I remember at Next New, folks thought we were crazy to program online video, which at the time was dominated by thinking about viral hits and one-offs, but it really remains as one of the tenets to building loyal audiences.

HW: Over the last five years, many celebrities have created their own YouTube channels or programming strategies. What’s the most common mistake they make? Anyone in particular surprise you with their ability to ‘go native’ to the platform?

VP: Biggest mistakes are thinking that if you post your content online your audiences will simply follow you. They’re looking to connect with the content, so if you’re not building your formats in ways that engage your community then you’re going to be ignored. There’s a reason why Late Night Talk Shows made the transition to YouTube online so well. Jamie Oliver and Karlie Kloss are also taking heed in what our endemic YouTube creators are doing – from collaborating with them to embracing native online formats. Ultimately we have witnessed over the last five years that the distance that mainstream media manufactured between a celebrity and fan has all but eroded online, community and the fostering of a direct connection is now everything.

I’m a total fanboy when it comes to great, tough reporters. Some of it stems from harboring fantasies of journalism as my “path not taken” but I also got to see the difference in skill levels from all the media covering Google/YouTube. The good ones are really good. The average ones are frustrating. Outside of the professional respect I hold for the good ones, they also have compelling personalities and backgrounds beyond the byline. Jessi Hempel and I have shared meals, hikes, drinks and panels. Here we share Five Questions…

Hunter Walk: Were you born a writer or did you become a writer? Either way, do you recall a specific moment when you thought “I want to do this as a career?”

Jessi Hempel: I was born a storyteller, but until the third grade, I was fairly confident I would be an ice skater. That year, I won the school writing contest for my essay on what I wanted to be when I grew up: though I had only been on ice skates once, I did a pretty good job of describing why it was the career for me. The principal handed me a trophy and told me I’d be a writer when I grew up, and it stuck. I believed her.

I studied creative writing in college, and was dismayed to discover, upon graduating, that it didn’t offer me a surefire way to pay my rent. I tried a bunch of jobs: I taught fourth grade, worked at a nonprofit, and made an ungodly amount of money doing odd jobs at a dot-com because hey, it was 1999. But I only wanted to write—the habit filled up all of my spare time, and eventually I understood that it was more of a calling than a profession. I was going to have to figure out how to do it all day, every day. So, I enrolled in the journalism program at the University of California at Berkeley.

HW: Early in your career you were a freelancer, but the last 12 years you’ve been a leading journalist at some great institutions (currently Wired; formerly Fortune, Businessweek). Besides a steady paycheck, what’s the value in being attached to a specific brand versus, for example, running your own shop a la Daring Fireball or Ben Thompson’s Stratechery?

JH: Over the past decade, I’ve seen the power relationship shift individual writers and brands. Individual bylines are more important than they used to be while big media brands don’t always have the strength they once did. This is happening, of course, not just in media, but across every industry. That said, I think we journalists can sometimes underestimate the power of traditional brands to provide strong platforms that amplify our voices and make us better journalists.

Wired’s digital platform had more than a billion unique readers last year; it also has the resources to support everything from the immense travel that went into this deeply reported feature on Facebook’s plan to wire the world to a new podcast that my buddy Tim Moynihan and I are preparing to launch. And most important, Wired has a community of creative, skilled editors and writers who make me better at my craft on every platform—these people really up my game.

HW: On some of the hot issues in tech – startup valuations for example – I’m sometimes surprised to see “techies” and “tech press” each assume a default position of opposing viewpoints. Is that a fair characterization in your mind? What’s changed over the last decade in terms of the role of the technology press? And why do tech workers seem thin-skinned (you can’t say “millennials”)?

JH: I think this varies widely from publication to publication, but that I have seen this gap widen as tech moves from its disruptor status in the economy to a more significant role as a primary engine of economic growth. The press has an important role to play in helping to hold technology companies accountable for the commitments they make to their shareholders, both public and private, and to their customers. That can create a productive tension that benefits the larger public.

And techies are thin-skinned, I won’t argue that. But I don’t know as they’re more thin-skinned than other business people who’ve been covered by the press over the past century. People react badly when you write things that depict them in a bad light, but if you say things are true, they almost always come around over time, and respect you more for it.

HW: You wrote “What We Need to Stop Talking About in 2016” — are there things you wished we talked MORE about in 2016?

JH: Yes! Yes, there are many things that I hope we talk more about. We need to help readers better understand the myriad ways in which companies are using their data—for the good, and for the bad. We need to do a better job of writing about where lofty valuations come from, what they represent, and how they will impact the longterm prospects of these companies, and the employees that work for them.

HW: Any recent pieces where you remembering thinking “Damn, that reporter can write!”

JH: There is so much awesome and smart writing right now! Like Fortune writer Erin Griffith’s profile of Nikesh Arora in which she opens with a description of a selfie swarm. Or my colleague Jason Tanz’ moving story about a man who built a video game about his son dying of cancer. And WIRED has an editor named Emily Dreyfuss who can clean up tough stories on security or business issues, and is also one of the funniest, smartest writers you’ll read. Check out her ode to Skymall, written as it filed for bankruptcy last year.

Obama was the first Presidential tenure of my adult life where I felt as if I could get involved and make a difference. During my time at YouTube, I saw a number of my former Google colleagues take roles on the campaign or in the administration. Mostly through these folks I was connected into a group of really brilliant, hard-working thinkers who saw new opportunities for public and private sector collaboration. Alec Ross, as a Senior Advisor to then-Secretary Clinton, struck me as someone who was willing to invest – and take risks – to make these partnerships work. His new book The Industries of the Future was published this week so I shot him five questions to answer for me. 

Hunter Walk: Your new book The Industries of the Future covers what’s going to happen over the next 10 years, especially areas of expected progress. What’s a point of view you’re taking that you’d consider contrarian? Any statement that people have especially challenged you on?

Alec Ross: I hope I’ve been aggressive enough with my thinking here that everybody will find something to disagree with. When two people agree on everything, it means that only one person is doing the thinking.

If there were one thing I’d flag, it’s my belief that the robots of the cartoons and movies of the 1970s will be the reality of the 2020s. I think the combination of powerful AI + cloud robotics  will give them the capabilities. By 2028 or so, advances in material sciences like air muscles (which distribute power through tubes holding highly concentrated pressurized air), electroactive polymers (which change a robot’s size and shape when stimulated by an electric field), and ferrofluids (basically magnetic fluids that facilitate more humanlike movement) will create robots that we might not even recognize as being artificial.

HW: I don’t mean to reveal book spoilers, but how does Silicon Valley fare? Does its historical advantage in technology innovation expand or contract in the next decade?

AR: I think Silicon Valley will continue to do very well and may do better than any other 30 mile long, 15 mile wide area on planet earth, but the geographic spread of innovation and wealth creation will be greater over the next 20 years than it has been over the last 20 years. This makes Silicon Valley’s % of ownership/domination relatively lower, but that’s not a bad thing. We should WANT more places to create wealth and well-being because, if nothing else, it gives us more people to sell stuff to. It also makes the world a more interesting and equitable place.

HW: We first met while you were working for Secretary Clinton and promoting “21st Century Statecraft.” Can you briefly explain what that meant and why you sent me to Iraq? 🙂

AR: My key thesis was that pinstriped foreign service officers needed help problem-solving and advancing America’s foreign policy interests in a world grown more driven by technology. The best way to do that was to bring in thinkers and do-ers from America’s technology sector and get them involved in our foreign policy. It was a huge success. Without getting into too many specifics here, we helped take down narcotics cartels in Mexico. We helped stop assassinations in the Middle East. We built the capacity of more than 1,800 civil society organizations working on issues ranging from women’s empowerment to clean water and election monitoring.

What the technology community needed was a way to get involved that made the highest and best use of their skills, and for four years we did that. It was a lot of fun and did a lot of good.

HW: If there was a particular ask you had of the technology industry with regards to its partnership with US government, what would it be?

AR: Help the government do a better job countering violent extremism. Nobody wants to hear it, but one of the biggest reasons Al Qaeda had to hide out in caves and recruit very secretly and ISIS is now controlling physical territory and recruiting overtly and effectively is because of technology. In Al Qaeda’s heyday there wasn’t social media or the proliferation of messaging apps and other tools that allow for frictionless communication and collaboration. I am not in favor of breaking crypto with mandatory backdoors and the like. I AM in favor of the technology community being a more serious and more engaged partner figuring out how to help dial back the radicalization that is taking place, enabled at least in part by our own technology.

HW: Given your history, I won’t ask you about any specific candidates this Presidential primary season but do you have a POV why “anti-establishment” messages seem to be resonating so strongly, at least in the poll numbers.

AR: I think there is a very high level of anxiety in America about the future. The lack of economic growth in the American middle class is entering into a near-record territory. Coupled with this anxiety is a sense of unfairness. There is a widely held perception that their economic stagnation is in large part because people at the top (the billionaires) and the bottom (new immigrants, people newly covered by Obamacare) are benefiting at their expense. The impulse to support fascists on the right or a socialist on the left comes from a very similar place.

You can purchase Alec’s new book The Industries of the Future on Amazon or at your local bookstore. 

Adam M. Grant’s new book Originals arrives today so seemed like a good time to ask him some questions. This past weekend Adam’s NYTimes post on How to Raise a Creative Child (hint: Back Off!) gave a taste of what Originals contains. My wife and I have been fortunate enough to know Adam for a few years now and always enjoy his thoughts on what makes people tick and what makes company cultures work (or not).

Hunter Walk: Your new book Originals is available starting today. What’s it about and how’d you settle on this topic versus other areas of interest?

Adam M. Grant: It’s about how individuals can champion new ideas and leaders can fight groupthink.  There’s a lot of guidance about how to generate creative ideas, but much less on what to do after you have an idea.  Think of this book as the sequel to creativity: it’s about how we can all get better at recognizing good ideas, speaking up, and finding allies.  I wrote it because students are constantly asking how they can make suggestions and pitch their ideas more effectively, and leaders are regularly seeking insight on how to battle conformity and drive innovation and change.

HW: What’s your writing technique like when you’re finishing a book? Do you force yourself to log a certain number of hours each day or pages each week?

AG: I used to follow a pretty rigid schedule: start writing in the morning, and don’t stop until I’ve finished a chapter or a major section.  Then I learned that procrastination can boost creativity, so while writing Originals, I taught myself to procrastinate.  At various points, I deliberately stopped in mid-sentence, leaving thoughts unfinished so I could come back to them with new ideas a few days later.

HW: Give and Take was a blockbuster and you’ve gained a ton of visibility with your writing and speaking. I’m sure a ton of offers get thrown your way. How do you balance the commercial opportunities vis a vis all the other parts of your life that you enjoy?

AG: I set a ceiling on the maximum number of speaking, consulting, and travel days I do per month.  When I go above it one month, I make up for it the next month.

HW: Is there a common misinterpretation of Give and Take that you hear from people?

AG: Yes—it’s not about how nice guys finish first.  I found that givers are overrepresented at the bottom and the top of most success metrics, so it would be more accurate to say that the book is about why some nice people finish last and others finish first.  But that’s not quite right either: being a giver is not about being nice. The goal is to help others, not please them.  There are lots of disagreeable givers out there—they’re gruff and tough on the surface, yet underneath have other people’s best interests at heart.  They give the critical feedback that no one wants to hear, but everyone needs to hear.  As a Google programmer described them, “They have a bad user interface but a great operating system.”

HW: When you compare Silicon Valley to the population at large, do we index differently on your Giver, Taker, Matcher segmentation?

AG: I would love to see rigorous data on that.  My experience has been that Silicon Valley has an unusually high number of people who act like givers for taker or matcher reasons.  It’s a small world where gossip travels as fast as the speed of sound, so many people try to get ahead by developing a reputation for generosity.  That’s not necessarily a bad thing, but there’s a difference between helping because you expect something in return and doing it because you enjoy helping others and seeing them succeed.  Ironically, when you give with the goal of getting ahead, it doesn’t work as well.

You can purchase Adam’s new book Originals at Amazon or your local bookstore