A chat with Natasha Mascarenhas, Reporter at TechCrunch

Journalism, Edtech, Fintech, Twitter, Tech vs Media, Diversity & more

October 20, 2020

Sar : I started following your work when you were at Crunchbase News covering startups and venture capital. Both of us moved to SF on a similar timeline. We became twitter friends and finally met in SF! I love reading your personal newsletter.

Anyhow, I have always been very curious about how young journalists go about building sources when they get started. Can you tell us how you started building your network of sources in Silicon Valley?

Natasha : Ah! I feel like the best compliment a writer can get is that their writing made someone else feel something, anything. So thank you for saying that, it really means a lot to me.

People make it seem like, in order to be successful, you need to be able to walk into a bar, schmooze your way into everyone baring their deepest darkest secrets, and tweet your way to virality. I really think it doesn’t have to be as calculated (or exhausting) as that. I think Mike Isaac got one of his biggest Uber scoops by sitting across from an employee at the bar and just listening.

So, I think in journalism it’s less about calculating what it takes to build a very successful source network, and more about how do you learn more from more people as time goes on?

Changing my perspective on that action-item has changed the game on how I grow the network of people I talk to for stories. I stopped viewing my empathy as a disadvantage, and started viewing it as a competitive advantage.

Anyways, my empathy-driven way of building up sources is scheduling a call with no purpose or angle other than getting to know each other better (this is not a rule for embargos or one-hit news pieces). Before the call, I prepare by learning about the person and getting a comfortable conversation opener. During the call, I take rough notes and try to straddle the line between being vulnerable, and being professional. My goal by the end of the conversation is not ever to make my source treat me like a friend, but instead treat me like a human they feel comfortable talking to.

It can be a time suck. Sometimes it doesn’t work. But the way this builds and gives me those returns is that at one point, I can start asking this source I have a colored perspective of about x, y, and z. In some cases, I’ll get some answers, in other cases, the media-training will kick in and they’ll pass, and in the best cases, they’ll answer x, y, and z, and then point me to the real story that lies in the a, b, c (I’m regretting this metaphor).

I think sources beget other sources, and stories beget stories.

Sar : Woah, I totally wasn’t expecting the direction you took with that question! I very much admire the mindset. You can tell how little I understand about how the sausage gets made in your world. My chat with Protocol’s Biz Carlson made that clearer to me last week.

You covered Clearbanc in the context of debt financing options when I used to work there! Now, that idea of alternative funding models is in vogue and is manifesting in different ways. Companies like Pipe are going after it for different business models like SaaS. There are capital arms of various companies like Toast, Stripe, Square, and Shopify. You have written about some of that as well. I'm sure you know twitter is all in on fintech memes. As a journalist who has some association with fintech stories, what can you tell us about common themes in fintech pitches you might be getting? What are some ideas or questions that are not fully hashed out enough for you to do a story but you often think about when you are staring at fintech domination in your inbox?

Natasha : If I had 20% more time in my week, I would cover fintech more rigorously because I think it’s a fascinating sector in technology right now (hot! takes! only!).

The idea that I think about a lot is how fintech is empowering the next generation of small-medium businesses, from the QR code we’ll find on tables to no such thing as cash-only establishments. I think a lot about Toast. The company made deep cuts in the beginning of the pandemic, but, going forward, it seems like it owns the key technology that the next generation of restaurants will need to adopt in order to be successful.

So I think that’s the crux of the next story we need to write about fintech: how will SMB services serve a forever changed business environment in post-covid dynamics. While Stripe and Shopify are obvious winners right now, I’m very excited to see what new entrants empower mom and pop shops going forward.

Sar : As you know, I have been working at the intersection of SMBs and technology for quite some time now. I would recommend GGV Capital’s piece and the Protocol’s Small Business Recovery series!

I have noticed you have significantly ramped up your coverage of edtech over the summer at TechCrunch. It is one of those areas where the pandemic has accelerated growth. You have written about everything from covering companies like CourseHero, Zoom for Class, BookClub to marco commentary on adoption, funding and learning pods & associated inequities. Looking back on the past 3-4 months, what are the biggest unclear questions in your mind based on everything you are seeing in edtech? What has surprised you the most?

Natasha : It’s crazy. My first day covering edtech was the day that Stanford closed classes. A one-off story became my informal beat here at TC, and I’m about to start a series on Extra Crunch looking at the future of different dynamics within education (so stay tuned)

The biggest unclear questions:

  • The growth of tutoring businesses is bringing, along with it, a spur of gig economy workers. We all know how gig economy workers have been exploited in other high-growth industries such as food delivery or ride-sharing, and so I’m curious how edtech plans to grow sustainably. How does the world of gig workers function in edtech and is it vulnerable to the same abuse in other industries?

  • I see a second digital divide coming. Before, it was between students who owned a laptop versus students who didn’t own a laptop. Now that more students have access to computers, there’s a new divide: who can afford to pay for supplemental services and who can’t? As teachers leave schools, this will become an even bigger dynamic.

  • Tests are going to go through a major upheaval.

The biggest surprises:

  • When I first started covering edtech, I made a list of the most interesting companies in the sector that raised money within the last year. Most of those companies raised during the pandemic, which eventually just felt like a game I was playing with myself. I wouldn’t count this as a subtle flex, but more so as an example of how many edtech companies really raised new money during this time.

  • The consumer habits in the United States continue to surprise me; families in China and India are more willing to spend for educational and supplemental services which is good news for edtech companies based there. While COVID-19 has forced American families to spend money, it’s still nowhere near China and India totals.

  • Re-skilling is an insanely huge industry that I snoozed before. It’s worth diving into.

Sar : I mostly agree with what you said. Connie Chen & Anne Lee Skates at a16z recently published a well researched edtech landscape piece. Here’s what they said with respect to the variance in spend across countries as you pointed out :

“Surprisingly, the amount of money spent on digital education in the U.S. still makes up a minuscule sliver of most state and school budgets, which are shrinking and famously tangled in bureaucracy. By comparison, we’re running behind countries like India and China. In China, online education is a $50+ billion industry, according to Deloitte, and is projected to more than triple in the next three years.

Meanwhile, in the U.S. COVID has brought renewed urgency to the mission to make our education system more digital and accessible. For many teachers and parents, the status quo—Zoomed-out kids passively watching teacher lectures—is sorely lacking.”

I want to now zoom out and talk about Twitter and Journalism.

Besides memes, a big part of being active on Twitter is discovering new people. We met on twitter! As a young journalist, what role do you think Twitter plays in your career? Do you think of Twitter as just a personal outlet that happens to help you with work every now and then or are you intentionally using it to find new stories, discover startups, etc?

Natasha : Twitter is a net positive in my life. When I was looking for a new opportunity while at Crunchbase News, I remember I DM’d the editor-in-chief of TechCrunch, Matthew Panzarino, over Twitter to catch up over coffee.

He was in preparation mode for Disrupt Berlin, but a month later, he reached out asking if I was open to chatting. As you can see, it worked out in my favor and I’m nearly 8 months into my job with TechCrunch!

I think that’s a fairly common story among those of us in tech, but it’s not lost on me how special it is that our world works that way.

My other favorite part of Twitter is that it lets me learn about people I wouldn’t otherwise meet. For example, you were one of my first Twitter friends! I met Freia Lobo and Kate Clark the same way. All of a sudden, the niche ecosystem I had moved across the country to work in did not feel so small. I started recognizing faces on Market Street and running into Twitter friends at dinners, and it was a refreshing dynamic. Another wacky, magical thing about Twitter that I’ll never take for granted.

The biggest problem with Twitter is that it twists tensions without context. And the job of a journalist is to explore different tensions that exist within the world and give them appropriate context. As a reporter in the beginning of my career, I constantly have to remind myself that Twitter isn’t tech. And tech isn’t Twitter. Panzer always tells us at TC to look critically at who we follow on Twitter; a diverse timeline is a diversity of thought, and I think that sometimes it ends up just being journalists talking to journalists, VCs talking to VCs, and founders talking to founders.

Sar : You are very engaged in tech twitter zeitgeist. Do you notice any changes in the conversations we are having and who is more visible on twitter these days? What would you like to see more or less of? Let’s avoid venturing into the tech vs media battle for now!

Natasha : The racial reckoning that happened this summer was a much-too-late awakening for the world, and the tech community. I think a lot of disturbing realizations were continuing to be had among the white supremacy that exists within venture capital and startups. I think those conversations should continue to exist.

I want the conversation and statements of support to move past Twitter, and into action, to lift and amplify Black entrepreneurs and investors. And of course, I’ll plug Megan Rose Dickey’s Human Capital, which is TC’s weekly newsletter for people who want to consistently educate themselves on topics about labor, diversity, and inclusion.

Beyond that, I think a lot about how Twitter has become the public square for all of us during this time. All of a sudden, we couldn’t run into friends at Blue Bottle or on the street or for happy hour. Twitter became the only place to really discuss and trade notes and talk; so it became even bigger in my daily routine. In its best moments, it’s a place where I can go to react and feel understood. In its lowest moments, it feels overwhelming to have the one place where you “run into” other people be filled with vitriol and hatred. All I can say is to limit your screen time, follow Karen Ho, and remember that a social media platform is not real life.

Sar : Alright, so tech vs media! I think most of the battle is basically a bunch of very online extremists on both sides fighting each other on Twitter scoring points for their tribes and the majority of people are just rolling eyes scrolling through their feeds. What are your thoughts on this never ending and often insufferable conversation? My generous read of the situation is it is often a clash of default optimism and default skepticism of the two sides. A lot of times, when you really see the specifics of the situation, it is a personal beefs masquerading as tech vs media.

Natasha : I think the real impact of the tech versus media “situation” is that stories that need to be told will not be told because of fear-mongering and a lack of education on how journalism works.

In the beginning of the pandemic, Zoom let us sneak into each other’s homes, see the frizzy truths of colleagues and sources, and at some points, made us skip the “I’m fine” small talk and go for the jugular of what’s hurting us. Then, something changed

I have seen vulnerability disappear from many, many founders I speak to. Remember the job of a journalist I mentioned above? To find tension and give context. While I still speak to some fantastic founders every single day, I have noticed media-training to a fault in more and more of the people I talk to. I don’t want to interview a walking, talking point. I want to interview someone who is candid. And part of me chalks up the new stoicism among a number of founders to a part of the tech versus media Twitter debate getting internalized by the next generation of founders.

But let me be clear, journalists are not victims of this dynamic. It all means that we need to work harder to be open about our processes and the way we work. No “gotcha journalism.” Make corrections when necessary. Think about context. Give grace to people who do not know how off the record works. I’m not going anywhere. Media isn’t going anywhere. We just need to react with empathy, and clarity.

Sar : That’s a very reasonable take!

You record a weekly podcast with your TechCrunch colleagues Alex and Danny. I am a fan. You guys make it both entertaining and informative. Do you find that there are some stories that are better suited for one medium or the other? Do you think tech journalism overall could explore doing audio-only stories for some topics? Audio adds a kind of color and tone that written word just cannot. I often feel the tech vs media battle could calm down a bit if we start humanizing people on both sides more. There are real people in the dunk tweets and uncomfortable stories! I always wonder about this when I see a journalist I follow do a live stream or a talk show on Clubhouse or goes on a podcast.

Natasha : Thank you!! I look forward to recording Equity each week because it gives me time to trade notes with colleagues I admire and crack a few jokes while doing so. I’d love to see more audio in tech journalism! I think it’s a good way to bring “reporter’s notebook” thinking to more people, and add a level of voice that doesn’t come off in stories. Imagine, a world in which tech could welcome and actually understand sarcasm!

I definitely would love to see tech journalism include more audio. And there’s a ton of rabbit holes we could go down here. For example, see this smashing piece by Casey Newton for where the world of audio journalism could be heading within tech. There’s also the services that share a news story in audio-form, and of course, podcasts. These all excite me, both from an accessibility perspective and, to your point, a color and tone perspective.

But, just like every form of content, audio requires a level of trust from the end-user. Equity listeners give us some of their mindspace, in this year nonetheless, twice a week. It can’t be taken lightly, and I feel like we need to consistently be innovating to make sure we’re not wasting anyone’s time. I think we do a great job, and I think we need to keep doing a great job.

Now, I’d love to say that audio, and Equity, was fixing the tech versus media battle. But, unfortunately, I don’t think we’re at that stage yet (spoiler alert, not everyone is good at taking jokes).

Sar : I'm sure you and most of my readers have heard of this idea of passion economy (my friend and prolific writer Li Jin coined that term when she was at a16z last year). A subset of that theme is journalists going independent. NYT’s Marc Tracy and Axios’s Sara Fischer did trend pieces on it in the wake of Casey Newton leaving Verge. Alex Kantrowitz & Anne Helen Petersen leaving Buzzfeed created a similar splash. There are many angles to explore here : what's hype vs whats real, newfound empathy for being a founder, relative cost-benefit analysis of being at a media company vs going solo, original content vs curation and commentary, etc. There are lots of hot, lukewarm and cold takes out there on each of these topics.

I wouldn't want us to regurgitate and relitigate them here. What I do want to riff on is the access and diversity angle here. There are many ways of thinking about it : 1) The role backgrounds, personality types and org cultures play in enabling journalists to build followings and personal brands on social media which later enables them to have the option to go solo. Will we see the Washington Post produce independent journalists, for example? It is well known for having stricter policies against social media usage. 2) Second angle to the diversity theme is it is just amazing to see the variety of content. There is something for everyone! But I do wonder if the conflation of writing well behind a paywall and reporting spreads more broadly! Journalism is a profession to be masterted just like any other! 3) The third angle is the shortage of practitioners in media of areas that are being written about. Will we see a wave of tech journalists going solo partnering up with people with the experience working at tech companies to give a better look at making sense of what's going on? There are obvious counter arguments here but this goes back to each side understanding the other better. Thoughts?

Natasha : This could be its own interview by itself, if you ask me. I discuss this a little in a post I just whipped up with the Equity crew a few days ago, but I think the future of media and journalism is complicated. There are a lot of good things that get me excited such as the opportunity for journalists to make more money, the opportunity for niche subjects to get the coverage they deserve (The Juggernaut, for one), and the opportunity for more people to write in general.

But, there’s a lot of realistic, not sexy aspects, that bum me about the “trend of journalists going independent.” Leaving a stable job to start a paid newsletter, for example, requires a level of wealth, platform, and audience. Often, that level of wealth, platform, and audience is only afforded to white dudes. The passion economy conversation often celebrates the wins, as it should, but ignores the inherent risk of going solo. Risk isn’t born equally. In fact, it’s a biased beast that disproportionately impacts black and brown people.

The reality is that outlets like the New York Times are still the dream for a lot of journalists. There are benefits when you work within a community, right down to being new and eavesdropping on the journalist you’ve admired for so long as they handle an upset source. I’ve truly learned so much that way -- My first big job in journalism was the Boston Globe and I got to sit next to Michael Rezendes, from the Spotlight team, every day. I wouldn’t trade that for anything. You learn a lot as a fly on the wall, and as I answer all these questions, I’m realizing that I should probably buy a shirt with this phrase or something because I can’t stop using it.

I worry that the glamorizing of going independent is being applied to all journalists, when in reality, only a handful of journalists within tech are trying it out. For the few that have, I will cheer them on with open arms and (when affordable) open wallets. But for the far other ones, you aren’t being boring.

Sar : I’m just going to leave this here :

Why do we not see journalists talk about stories they could have written but didn’t? Is there a journalistic code against this?

Natasha : This has happened to every journalist, millions of times, and usually it just ends up being a retweet and a salty, fake-jealous, slack message to your work friend. There’s no journalistic code against tweeting it openly that I know of, but I usually stick to being a good sport and giving the reporter kudos. I think it’s a little self indulgent to say that you had an idea while there’s some out there who executed on that same idea before you did.

Speaking of codes though, I think one of the biggest journalistic codes which certain publications don’t follow (and we all know who those are), is linking stories from other outlets if you get the information from them. Link! Link! Link! I worked at a small media startup, and I saw first-hand how much of a difference it makes in both confidence and traffic to be properly cited for your work.

Sar : I'm a big believer in supporting the good work of people who don’t have high profiles. Too often the twitter zeitgeist gets obsessed with certain things because of the popularity of people behind those things. Who are the 5-10 under-the-radar journalists we should check out and support?

Natasha :

Previous interviews :