Dropbox had a blockbuster IPO and is now worth $13 billion — now the exec who led its growth explains what comes next (DBX)

Dennis Woodside

  • Dropbox had its long-awaited IPO on Friday — and had a huge pop of almost 36% in first-day trading.
  • Dropbox COO Dennis Woodside, largely credited with leading the cloud storage company to growth, sat down with Business Insider for an interview. 
  • In the interview, Woodside discussed what investors didn’t understand about Dropbox, why it doesn’t like being called an enterprise company, and how the company reminds him a lot of his days at a pre-IPO Google Google.


NEW YORK CITY — Another San Francisco unicorn made the trip to Wall Street on Friday, as the 11-year-old cloud storage company Dropbox debuted as a public company. 

Dropbox’s $9.2 billion IPO was widely anticipated, on both coasts. And it had a first-day pop of almost 36%, with the stock worth $28.48 at the closing bell. 

But with the champagne all poured out and the confetti settled, it’s time for the company to get down to business and start working toward maturity — not to mention profitability. 

Leading that charge is Dennis Woodside, who joined Dropbox as chief operating officer in 2014, after a stint as CEO of Motorola. Woodside is largely credited with helping Dropbox mature its business, and spearheaded its push into business and enterprise sales. 

Business Insider’s Becky Peterson sat down with Woodside at the NASDAQ in Time Square to hear about his thoughts on Dropbox’s future, Silicon Valley, and the changing nature of technology for businesses. He shared his thoughts on profitability, growth, why he doesn’t like it when Dropbox is called an “enterprise” company, and how Dropbox reminds him a lot of his experiences at at pre-IPO Google.

Here are some highlights from the interview. 

‘Storage is really a starting point for a much broader opportunity that we’re focused on’

Peterson: I’ve heard that from other executives, […] that the IPO is not the finish line. What is the finish line for you?

Woodside: Well if you think about the state of the world, the state of cloud, and the state of work today, we see lots of problems that are unsolved.

The first one, that we’re focused the most on, is around enabling teams to collaborate regardless of what operating system they have, what device they have, around their most important intellectual property, which often is a file.

The Golden State Warriors — they have to collaborate around scouting reports, and they do all that in Dropbox. Or Expedia has to collaborate with its hotel partners around photography or imagery that’s going to go on their site, and that all happens on Dropbox. So that’s a big problem.

We think it’s still pretty early in the adoption of cloud generally. More than three quarters of our users are outside of the US. There is a big international opportunity, just with Dropbox, the product we all know and love. And then we see opportunities in collaboration around that content, and the first product that indicates the direction we’re excited about is Paper.

Paper is a collaborative text editing tool. It’s super easy to embed anything in your Dropbox into a Paper. And teams like the team that produces Saturday Night Life use paper to produce that show. They’re embedding images of wardrobe and video cuts and project cuts. It’s a much more 2018 way of working together than a lot of the other tools that are out there.

So that’s where we’re heading — How do we enable teams to be more effective and creative through technology?

Peterson: So you’re looking more at growing your collaboration tools than enterprise storage?

Woodside: Our business certainly started out as, “let’s move all files to the cloud so that you can access them anywhere.” But we really don’t get paid for that. There are other solutions that provide that. We get paid for the collaborative elements of Dropbox. For sharing content, enabling you to view content on any device. For all the integrations that we’ve built with Salesforce and Autodesk and Microsoft products. So it’s super seamless to pull a document from Dropbox and work on it, and get some work done.

Storage is really a starting point for a much broader opportunity that we’re focused on. We’ve built the enterprise “grade” security features, functionality controls. Those are table stakes to be able to compete in larger and larger businesses, but that’s not necessarily what’s going to drive users to move to Dropbox. So we focus on the end user. We deliver value for that end user. Of course we can provide the security that IT needs, but it’s that end user focus that differentiates us.

Dropbox isn’t profitable but it’s fully committed to its free service tier

Peterson: Dropbox has a freemium model for consumers. We see this at Spotify too, which is also going public soon, where neither company is profitable, and you both have this freemium model. Do you think that’s a necessary part of your business model, or do you ever see Dropbox phasing out that model?

Woodside: The 500 million registered users are important to us. They create network effects that are how we grow. People sign up for Dropbox. Usually they find out about it from a friend. Then they share a file with another friend and that friend signs up. What happens in many businesses, you already have many people using Dropbox as an informal solution before they even pay us. So those users effectively are sales people over time. And that enables us to spend less on sales and marketing than our competitors. 

And the good news is, the cost of serving them that fundamental storage over time declines, which is why we’ve been able to expand our gross margins and drive 28% free cash flow margins, which is remarkable for a business of our scale and our growth.

‘Be worthy of trust’

Peterson: You joined Dropbox in 2014. How has the company changed? Are there any big programs that you think have been important in your time there?

Woodside: We’ve grown a lot. We were about 500 people then and now we’re about 2,000. Revenue has roughly quadrupled. From a business standpoint, Dropbox Business existed and was pretty nascent. We had not built some of the controls that were required to compete in larger and larger teams. So we have done that and obviously we’re winning in the market lots of larger companies.

I think from a cultural standpoint, Drew and Arash have been really focused on preserving the culture, codifying the values, trying to make sure that as we grow, we don’t lose touch with those values.

And that goes from who do we hire, to who do we promote, to how do we evaluate people?

Peterson: Can you share what those values are?

Woodside: I’ll share a couple. One of them, and one of the most important one, is be worthy of trust. If you think about our business, people are entrusting us with their most important information. It could be project plans, or videos related to Saturday Night Live. and we have to be worthy of their truth in how we secure that information and access that information at all points in time. That’s been fundamental to the business.

Another one is aim higher, so always be stretching yourself, stretching your team, trying to deliver experiences that are magical, and surprising and helpful and delightful. And that also informs our product vision. And we think Paper is that kind of experience where you ind of discover things along the way that you wouldn’t have expected the product can do.

Dropbox straddles the line between consumer and enterprise

Peterson: Is there anything about the Dropbox story that you think surprised investors?

Woodside: I think it’s not as well  understood that our business, our future, and what we deliver today is about really enhancing the work experience and allowing people to collaborate around content. I think it did surprise people that we have four billion pieces of content, we have a billion AutoCAD files, we have billions of Office docs, and we have 500,000 developers working on the Dropbox platform that integrate Dropbox into all kinds of workflows I think some people who haven’t followed the story for a long period of time think of us as that consumer company that we started out as.

People like to put you neatly in the consumer box or in the enterprise box. We kind of transcend that in that we have this viral model of attracting users. Those users bring us into businesses and then the real value is in that business use case. And that also our business model — which is highly predictable and really is a software-as-a-service model. So that story is for more sophisticated investors who have followed us, they get it.  But for others who are newer to us, it was definitely good to have a roadshow and to have those conversations and educate people.

Peterson: Were investors under the impression that Dropbox has an unpredictable business model?

Woodside: If your view of Dropbox was 2014, where the majority of the focus was on a more consumer use case — if that was still your vantage point then you might not have appreciated the traction that we’ve gotten in businesses. The fact that we have 300,000 paying teams which if you look at the scale of that, we added 80,000 teams in the last year, and Box has 80,000 and they’ve been at it a lot longer than we have.

We’ve added these huge accounts and if you were more of a casual observer of the story, you might not have realized that. The misconception was that we’re consumer, not business focused.

Dropbox doesn’t like being called an enterprise tech company

Peterson: Do you think it’s accurate to say that enterprise is the only way for you to reach profitability?

Woodside: The word “enterprise,” to be honest, we don’t like. Because it implies very big companies, where as we are able to profitably reach small and large businesses all around the world. And it’s rare that companies can do that. If you think about who has been able to profitably reach a five person company as well as 30,000 seat deployment, there’s not a lot. There’s in the ad business Facebook and Google. In the infrastructure business, Amazon. And it’s this self-serve model that we built that educates people when they’re in the free product and helps them understand the work use case so they take us into work. That’s a very unique approach. So we try not to categorize ourselves because at the end of the day we’re serving people at work, and some of them are in very small organizations and some of them are in huge organizations.

Dropbox is run a lot like Google was before it went public

Peterson: Let’s go back to company culture. I know you spent a lot of time at Google. How would you compare the two companies in terms of style and management?

Woodside: I started at Google in 2003, so before Google’s IPO. I want to say there were under 1,000 people at the time, so small than Dropbox is now. I want to say that there are some similarities in that both companies are led by deeply technical, product-oriented founders, and I think that’s super important in a technology company. You need that focus on what can technology do? How can it solve a real problem for people. You need that beating heart of innovation in your leadership and for both companies, the founder-led leadership team is super important as well because you have two people in Drew and Arash here who  have their heart in the business and they’re going to be in it for a long time, and they deeply care about the customers and people here. And that was true at Google as well.

Now, different time, different place, and different competitive environment. All of those things are quite different.

Sexual harassment and discrimination are ‘competitive disadvantages’

Peterson: What do you think Dropbox’s biggest challenges are in the next five years?

Woodside: We don’t have limitless resources so we have to pick our battles well. We’ve done a good job in the last couple of years, like when we moved to our own infrastructure, we did that well. Now we have Paper, and we’ve proven that the product is delightful and solves problems, and we need to get more people using Paper. That’s the next set of challenges ahead of us.

SEE ALSO: Dropbox made its trading debut Friday as the most prominent tech IPO in 2018

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The Cambridge Analytica data probably isn’t on the dark web — but more dangerous personal information might be

Dark Web Thumb 2x1

  • Security experts told Business Insider that data obtained by Cambridge Analytica isn’t likely on the dark web.
  • But there is a larger problem with how much personal data is exposed online, either by legitimate companies looking to sell ads, or by hackers.

The type of personality data harvested by Cambridge Analytica might allow researchers to predict who someone might vote for, but it pales in comparison to what data advertisers collect or what sensitive data is for sale on the dark web.

“The Cambridge Analytica thing has really resonated with people, but it has pointed out a much larger problem,” Mark Turnage, the CEO of DarkOwl, a cybersecurity firm specializing in the dark web, told Business Insider. “The more websites you use the more careful you have to be, because that data is not only being bought and sold for perfectly legal uses, but it’s also being bought and sold for illegal uses.” 

The scope of how much data is being brokered between companies and cyber criminals online has been a concern for privacy advocates for years; everything you do online is tracked some way or another. 

Advertisers, social media companies, and e-commerce websites not only track what users do on their own platforms, but they use cookies to track what other websites or applications users visit.

“If people really knew how much data was used for companies to learn about them, track them, and sell products to people, they’d probably be a little more careful with their data,” said Corey Milligan, a senior threat analyst at cybersecurity firm Armor.

And that’s just what’s legal. Hackers also use malware to target companies and public institutions that store social security numbers, credit card numbers, bank account information, health records, and login information to various websites.

The marketplace for personal data on the dark web — the part of the internet not indexed by search engines — is so big it’s almost impossible for security researchers to quantify just how many records are out there.

But it’s unlikely the Cambridge Analytica data, which was improperly obtained from 50 million Facebook users, has made its way on the dark web. The UK-based firm used the data internally, so unless hackers stole it from Cambridge Analytica, the data probably isn’t for sale, security experts told Business Insider

Plus, the types of “psychographic” data likely obtained from Facebook — where you live, your likes, dislikes, relationship status, birthday — aren’t as valuable to hackers as the sensitive financial and health records that could be used to steal someone’s identity.

“I haven’t seen psychographic data on the dark net, and the reason for that is because if you think about a criminal who is buying data, their desire is to get access to data that can be immediately monetized,” Turnage told Business Insider.

While social security and credit card numbers might be more dangerous than the data Cambridge Analytica obtained, the consequences of the debacle have been swift and far reaching. The scandal has spawned #deletefacebook, outraged users, caused lawmakers to call on Facebook CEO Mark Zuckerberg to testify, and dramatically dropped Facebook’s stock price.

Turnage said this is due to the divisive political nature of the debacle.

“People don’t like to feel that someone is trying to manipulate them in a particularly underhanded way,” Turnage said. “Campaigns run political ads all the time, that’s part of the process — but stealing data and sending articles to try and influence people’s political opinions crosses an emotional line.”

SEE ALSO: A Facebook shareholder launched a lawsuit against the social network over the Cambridge Analytica scandal

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Cloud computing has caused a huge spike in the demand for data centers

With the surge of cloud computing, there’s been an increase in demand for more and more data centers. While many might visualize “the cloud” as an intangible asset that lives online, these terabytes of data are stored in vast warehouses that are taking up a growing amount of physical space.

As the need for data centers grows, so does the amount of money invested in them. This chart by Statista shows the gradual increase of money invested in data centers in North America over the past six years, which spiked in 2017 at a staggering $20 billion. 

Chart of the Day

SEE ALSO: Most Facebook users believe Facebook will have a negative impact on society within 10 years Most Facebook users believe Facebook will have a negative impact on society within 10 years

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This private club of socially-conscious entrepreneurs bought a ski mountain in Utah for $40 million to build what has been called a ‘utopia for the millennial elite’

Powder Mountain Summit

  • Summit, a socially conscious entrepreneurial collective, bought a mountain in Utah in 2013 for $40 million.
  • The community is known for its progressive events with leaders at the forefront of their respective industries making up the attendee list.
  • Summit has begun building 28 houses on Powder Mountain as a first step toward providing a more permanent location for its followers.


On Utah’s Powder Mountain, you’ll find some of the world’s most influential individuals on what has been dubbed “the utopia of the millennial elite.”

The socially conscious entrepreneurial community Summit, founded in 2008, purchased the mountain for $40 million in 2013, adding it to its repertoire of elite meeting grounds.

The collective is known for hosting gatherings designed to cultivate the biggest and brightest ideas of the millennial generation by bringing together leaders at the forefront of their respective industries. Richard Branson and Sophia Bush count themselves among the Summit clan, and anyone wanting to join must go through an application process beforehand.

Summit, which has been described as a mix of Ted Talks and Burning Man, is taking its progressive programming to the slopes. According to a report published in The Guardian, Summit’s founders envision that the mountain will bring together its community members in a more permanent settlement. 

Powder Mountain is still under construction, but these photos give us an early peak inside the Utah utopia. Take a look.

SEE ALSO: Silicon Valley loves Burning Man and these tech executives are no exception

Welcome to Powder Mountain.

It’s the largest skiable resort by acreage in the United States.


The closest city is Eden, Utah, at seven miles away. Salt Lake City sits 55 miles south.

See the rest of the story at Business Insider

Jim Carrey has taken his criticism of Trump to a new level with a sexually explicit drawing of the president

Jim carrey

  • Actor Jim Carrey has taken his Twitter and artistic war with President Trump to a new, sexually explicit level.
  • The latest drawing, posted to Twitter Friday, features Trump in bed with a woman who is presumably adult film star Stormy Daniels.
  • Carrey has courted controversy this week over other drawings he has posted to Twitter, including an unflattering depiction of White House Press Secretary Sarah Huckabee Sanders.


Actor Jim Carrey isn’t backing down from his criticism of President Trump — and he’s now taken it to a new level.

On Friday, Carrey tweeted a drawing that depicts Trump in bed with a woman who is presumably porn actress Stormy Daniels. Daniels has recently been at the center of a legal battle with Trump and allegedly had an affair with the president in 2006.

Carrey covered the most explicit areas of the drawing with the Presidential Seal, and included the caption “Fifty Shades of Decay.”



Trump allegedly began having an affair with Daniels in 2006 when current First Lady Melania had just given birth to their son, Barron. Daniels sued Trump earlier this month, claiming that Trump never signed a nondisclosure agreement intended to prevent her from talking about the alleged affair.

Carrey himself has been the subject of some controversy this week for other drawings he tweeted. The actor has become an unlikely political artist and activist on Twitter, and has been quite busy over the past several days.

On Saturday, Carrey tweeted an unflattering image of White House Press Secretary Sarah Huckabee Sanders that called her Christianity into question and received backlash from conservatives, including on Fox News.



Carrey was unfazed by the criticism, telling The Young Turks in a statement that he was “so gratified by the reaction to my little drawings.”

He followed that drawing up with one that portrayed Trump as the “Wicked Witch of the West Wing.”

SEE ALSO: Jim Carrey slams Mark Zuckerberg in a new portrait: ‘Who are you sharing your life with? #regulatefacebook’

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An Army sergeant explains why you don’t want to see the massive M777 howitzer lowered all the way down

155mm howitzer army

  • We saw an M777 howitzer lowered all the way to the ground.
  • An Army sergeant explained that the only time it’s lowered all the way is when the enemy is close.
  • “If you’re receiving contact on this howitzer, that means all your front lines are not there anymore,” he said.

FORT BLISS, Texas — At one point, as the soldiers above were showing me around the massive M777 howitzer, they lowered it all the way down so that it was parallel to the ground.

Given that the howitzer is meant for support, I was asked why and in what situation they would need to lower it that far down.

Sgt. Shaw, who has served in Iraq and Afghanistan, told me the only time it’s lowered all the way is when the enemy is close — not a good position to be in, given that the cannon is meant for support.

Shaw said his crew once took contact when he was in Afghanistan, but he understandably didn’t want to go into detail.

“If you’re receiving contact on this howitzer, that means all your front lines are not there anymore, or they’ve been able to flank the infantry,” he said.

army soldier m777 howitzer

Operated by a crew of eight to 10, the Triple 7 howitzer fires 155mm precision and non-precision munitions.

The non-precision guided munitions have a maximum range of 18.6 miles, while the Excalibur precision-guided rounds have a maximum range of 25 miles and are accurate to within 30 feet.

The howitzer can also fire up to five rounds per minute, or two rounds per minute sustained.

During one deployment to Afghanistan, Shaw said his crew fired the howitzer while lowered at the enemy eight to 10 miles away. 

So even when completely lowered, the Triple 7 still has range. 

SEE ALSO: This is the huge M777 howitzer that US Marines burned out while fighting ISIS in Syria

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We drove a $63,000 RAM 1500 pickup truck to see why it’s part of America’s latest obsession — here’s the verdict (FCAU)

RAM 1500

  • The RAM full-size pickup is the perennial third-best-seller in the US, behind the Ford F-150 and the Chevy Silverado.
  • We spent a week with a well-appointed version of the truck.
  • And we were mighty impressed.

We certainly live in a Golden Age for luxury pickups, which are becoming America’s latest obsession. Detroit can’t sell enough of them. In the first two months of 2018, Ford has already moved 127,000 F-150s. And everything truly is better. That gas-chugging V8 on a ’78 Chevy would give you just about 160 horsepower, while a modern V8-motored pickup will top 400hp with better fuel economy. It’s also hooked up to the internet, is far more reliable, and can be had with all manner of luxurious appointments. 

Ford has revamped its segment-leading F-Series pickups, and now both Chevy/GMC and Fiat Chrysler’s RAM have followed suit. For old time’s sake, however, we jumped at the chance to sample the outgoing RAM 1500 when the carmaker flipped us the keys to a well-optioned $63,870 2018 Limited Crew Car 4×4 version of the third-best selling pickup in the USA (over half a million units in 2017).

Here’s how it went.

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The RAM 1500 Limited Crew Cab 4X4 has a base price of $53,595, which is a lot higher than the stripped-down $27,000 no-frills trim level. Our “Maximum Steel Metallic” tester stickered at $63,870.

The RAM 1500 is a full-size pickup — the heart of the pickup market. These trucks have to be able to do it all, from hauling stuff to towing stuff to driving people around.

RAM pickups have a more aggressive, semi-truck-like appearance than the competition. It isn’t for everybody — but we thought it make our tester look pretty imposing.

That’s a “Tungsten Chrome” grille, by the way. Which means it isn’t shiny chrome. And it looks pretty fantastic.

See the rest of the story at Business Insider