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Dropbox CEO Drew Houston speaks onstage during the Dropbox Work In Progress Conference at Pier 48 on September 25, 2019 in San Francisco

Matt Winkelmeyer | Dropbox | Getty Images

In this weekly series, CNBC takes a look at companies that made the inaugural Disruptor 50 list, 10 years later.

One year after graduating from MIT in 2006, Drew Houston began working with Arash Ferdowsi in hopes of creating one of the first cloud-based file sharing platforms that would eliminate the annoyances of physical thumb drives. The result was Dropbox, a company that has now made a name for itself as one of the leading organization and collaboration tools worldwide.

Today, Dropbox reports having more than 700 million registered users in more than 180 countries and regions globally. The company brought in $2.2 billion worth of revenue in 2021 and is a five-time CNBC Disruptor 50 company.

With goals to reduce busywork and help organizations stay in sync, Dropbox offers a suite of systems that include cloud storage platforms, password managers and computer backup systems. It has grown its offerings in acquiring platforms such as HelloSign in January 2019, Valt in November 2019 and DocSend in March 2021.

In its most recent quarter, Dropbox reported $591 million in revenue with a net profit of $83.2 million. Over 17.5 million users pay for its services, and the company has said more than 90% of its revenue results from individual consumers buying subscriptions. 

“In particular, we’re pleased with the results of the changes to our team’s plans, and excited about our progress innovating around new products and driving multi product adoption, including the release of Capture to all Dropbox users and the introduction of the rebranded Dropbox Sign,” Houston, who is now Dropbox’s CEO, said in a statement. “As we look towards 2023 and beyond, I’m proud of our team’s execution towards our strategy while maintaining a healthy balance of growth and profitability.”

Dropbox went public in March 2018, listing a highly-anticipated $756 million IPO on the Nasdaq. One of the largest IPOs in tech at the time, Dropbox was valued at more than $12 billion on its first day of trading. Its performance since an initial surge has been rocky.

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As one of the first companies to embrace the shift to a virtual workplace at the beginning of the pandemic, Dropbox announced its “virtual first” remote work setup in October 2020, asking employees to work remotely 90% of the time. The program, which officially launched in April 2021, was a significant shift for the business that once flaunted perks like award-winning cuisine in its cafeteria, and a top-notch gym and yoga studio, all at no cost for employees. The change also cost the San Francisco-based company almost $400 million in real estate, turning it unprofitable in the fourth quarter of 2021.

Even with some reports that the business is seeing high turnover rates attributed to the previous in-office bonuses being taken away, Dropbox has picked up on “boomerang” employees, bringing many previous employees back to the company on account of the workplace flexibility it now offers, Houston said at the CNBC Work Summit in October.

“We’ve been able to punch way above our weight class,” Houston said at the CNBC Work Summit. “I think the companies who offer that flexibility are going to be able to outrecruit, outretain, outperform ones that don’t.”

Dropbox continues to face many competitors in the cloud space – Google, Microsoft and Apple, to name a few of the most notable, as well as fellow former startup to IPO, Box. The company is forecasting revenue of $2.3 billion for 2022 and foresees revenue between $592 million and $595 million for the fourth quarter. But the stock remains well below its first-day trade from back in 2018, and at roughly half the value of its highest market peak, caught up in the tech downturn that has cratered many former high-flying, high growth startups.

“We’ve always lived in a competitive environment … and importantly all our growth has happened in that environment,” Houston said at the time of the Dropbox IPO. “We don’t see Amazon in our space. You know, things can change. We don’t count anyone out.”

To create long-term value, Dropbox is building on momentum through promoting new products and acquisitions, Houston said on CNBC’s “TechCheck” in November 2021. The company plans to introduce more of its products to existing customers in hopes of increasing the number of paid users on its platform, Houston said.

“We certainly made a lot of progress since we went public, and we have a lot of opportunity in front of us,” Houston told TechCheck.

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French fintech Pennylane doubles valuation to $2.2 billion as Alphabet’s venture capital arm takes stake

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French fintech Pennylane doubles valuation to .2 billion as Alphabet's venture capital arm takes stake

Seksan Mongkhonkhamsao | Moment | Getty Images

French accounting software firm Pennylane has doubled its valuation to 2 billion euros ($2.16 billion) in a new 75 million euro funding round.

Pennylane told CNBC that it raised the fresh funds from a host of venture funds, with Sequoia Capital leading the round and Alphabet’s CapitalG, Meritech and DST Global also participating.

Founded in 2020, Pennylane sells what it calls an “all-in-one” accounting platform that’s used by accountants and other financial professionals.

The platform is primarily targeted toward small to medium-sized firms, offering tools for functions spanning expensing, invoicing, cash flow management and financial forecasting.

“We came in tailoring a product that looks a bit like [Intuit’s] QuickBooks or Xero but adapting it to the needs of continental accountants, starting with France,” Pennylane’s CEO and co-founder Arthur Waller told CNBC.

Pennylane currently serves around 4,500 accounting firms and more than 350,000 small and medium-sized enterprises. The startup was previously valued at 1 billion euros in a 2024 investment round.

European expansion

For now, Pennylane only operates in France. However, after the new fundraise, the startup now plans to expand its services across Europe — starting with Germany in the summer.

“It’s going to be a lot of work. It took us approximately five years to have a product mature in France,” Waller said, adding that he hopes to reach product maturity in Germany in a shorter time period of two years.

Pennylane plans to end the year on about 100 million euros of annual recurring revenue — a measure of annual revenue generated from subscriptions that renew each year.

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“We are going to get breakeven by end of the year,” Waller said, adding that Pennylane runs on lower customer acquisition costs than other fintechs. “75% of our costs are R&D [research and development],” he added.

Pennylane also plans to boost hiring after the new funding round. It is looking to grow to 800 employees by the end of 2025, up from 550 currently.

‘Co-pilot’ for accountants

Like many other fintechs, Pennylane is embracing artificial intelligence. Waller said the startup is using the technology to help clients automate bookkeeping and free up time for other things like advisory services.

“Because we have a modern tech stack, we’re able to embed all kinds of AI, but also GenAI, into the product,” Waller told CNBC. “We’re really trying to build a ‘co-pilot’ for the accountant.”

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He added that new electronic invoicing regulations coming into force across Europe are pushing more and more firms to consider new digital products to serve their accounting needs.

“Every business in France within a year from now will have to chose a product operator to issue and receive invoices,” Waller said, calling e-invoicing a “huge market.”

Luciana Lixandru, a partner at Sequoia who sits on the board of Pennylane, said the reforms represent a “massive market opportunity” as the accounting industry is still catching up in terms of digitization.

“The reality is the market is very fragmented,” Lixandru told CNBC via email. “In each country there are one or two decades-old incumbents, and few options that serve both SMBs and their accountants.”

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TikTok reportedly stays on App Store after assurance from Attorney General Pam Bondi

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TikTok reportedly stays on App Store after assurance from Attorney General Pam Bondi

In this photo illustration, the logo of TikTok is displayed on a smartphone screen on April 5, 2025 in Shanghai, China. 

Vcg | Visual China Group | Getty Images

Apple will keep ByteDance-owned TikTok on its App Store for at least 75 more days after receiving assurances from Attorney General Pam Bondi, according to a report from Bloomberg News.

This comes after President Donald Trump signed an executive order Friday to extend the TikTok ban deadline for the second time. TikTok will be banned in the U.S. unless China’s ByteDance sells its U.S. operations under a national security law signed by former President Joe Biden in April 2024.

AG Bondi wrote in a letter to Apple that the company should act in accordance with Trump’s deadline extension and that it would not be penalized for hosting the platform, according to unnamed sources cited in the report.

Apple did not respond to a request for comment.

After TikTok went briefly offline for U.S. users in January following the initial ban deadline, it remained unavailable for download in the App Store until Feb. 13. Apple had reinstated TikTok to its app store after receiving a similar letter of assurance from Bondi.

The extension comes days after Trump announced cumulative tariffs of 54% on China. Prior to the additional tariff rollout on April 2, the president said he could reduce duties on the country to help facilitate a deal for ByteDance to sell its U.S. operations of TikTok.

“Maybe I’ll give them a little reduction in tariffs or something to get it done,” Trump said during a press conference in March. “TikTok is big, but every point in tariffs is worth more than TikTok.”

WATCH: TikTok deal reportedly halted after China said it would reject it due to tariffs

TikTok deal reportedly halted after China said it would reject it due to tariffs

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For bitcoin bulls who self-custody crypto, the global risks are growing

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For bitcoin bulls who self-custody crypto, the global risks are growing

Whether to buy cryptocurrency as a long-term holding may be the biggest decision an investor interested in digital assets has to make, but where to store crypto like bitcoin can become the most consequential.

Following the wildfires earlier this year in California, social media posts began to appear with claims of bitcoin losses, with some users showing metal plates intended to protect seed phrases burnt up and illegible or describing the complexity of recovering crypto keys stored in a safety deposit box in a bank impacted by the fires. While impossible to verify individual claims about fires consuming hard drives, laptops and other storage devices containing so-called hard and cold storage crypto wallets and seed phrases, what is certain is that bitcoin self-custody presents a unique set of security issues. And those risks are growing.

Holders of crypto typically use some form of what can be called a “wallet,” and there are a few main features – whether that wallet is connected to the internet, and how much control is directly embedded in the wallet for trades and transfers. There is also the underlying issue of whether a crypto investor uses a third party for custody at all, or maintains total custody and trading control over their holdings.

The standard third-party platform “hot wallet” – think of an offering from a Coinbase or Blockchain.com – is constantly connected to the internet. Cold storage and “cold wallets,” on the other hand, include hardware devices (like a USB stick) that holds private keys offline, or even just a seed phrase (a master recovery code, a collection of 12 to 24 words used to recover access to a crypto wallet) on paper/metal. Hardware wallets or offline backups of seed phrases can be used to access crypto when connected to the internet through another device.

With third-party custodial options, there are steps to help owners remain vigilant against the threat posed by cybercriminals who can gain access to an internet-connected platform, including the use of two-factor authentication, and strong passwords. The U.S. Marshals Service within the Department of Justice, which is responsible for asset forfeiture from U.S. law enforcement, uses Coinbase Prime to provide custody for its seized digital assets.

Many crypto bulls prefer to self-custody digital assets like bitcoin for some of the same reasons they are interested in cryptocurrencies to begin with: lack of faith in some forms of institutional control. Custodial wallets from crypto brokers trade convenience for the risk of exchange hacks, shutdowns, or fraud, as in the case of the high-profile implosion of FTX. And the wildfires are just one example in a recent string of global events that raise more questions about shifts in the crypto custody debate. There is the ongoing conflict in the Middle East and Russia-Ukraine war, which has led crypto bulls from overseas to re-think their approach to self-custody.

Nick Neuman, co-founder and CEO of self-custody company Casa, said physical risks in the world like a natural disaster are an opportunity to revisit how bitcoin security works, and the common security lapses folded into most peoples’ practices. “Most people secure their bitcoin with one private key. If that key is on a single device or written down on paper as a seed phrase, it’s a single point of failure. If you lose that key, your bitcoin is gone,” he said.

It should be obvious that keeping seed phrases on paper offers the lowest level of protection against fire, yet it is common practice, Neuman said. Slipping these pieces of paper into fireproof bags or safes offer some protection, but not much, and even going the extra steps to have the seed phrases on “indestructible” metal storage plates presents a few failure points. For one, they might prove to be not so indestructible, and second, they may be impossible to locate amid the rubble. 

“Logically, given the location of the fires in California and the stories being shared on X, it’s highly likely bitcoin was lost,” said Neuman. “Some of them are pretty convincing,” he said.

Casa performs annual stress tests on seed phrase backups.

Some self-custody services, like Casa, offer multi-signature setups that reduce the risks of single-point failure. A multi-key crypto “vault” can include mobile phone keys, multiple hardware keys, and a recovery key that a company likes Casa holds on an owner’s behalf.

The multi-sig custody approach allows an owner to hold a majority of keys while a trusted partner holds a minority of keys. John Haar, managing director at Swan Bitcoin, says that in such a setup, the owner would need to lose all the physical devices and all copies of the seed phrases at the same time. As long as the owner can access at least one device or one seed phrase, they would be able to recover their bitcoin. This approach should significantly limit the potential for all of the devices to be lost in an event like a natural disaster, Haar said.

“You can spread these keys across multiple regions or even countries, and you need any three of the five keys to approve a bitcoin transaction,” Neuman said of Casa’s five-key approach.

Jordan Baltazor, chief administrative officer at Fortress Trust, a regulated crypto custodian, says best practices that we use in other areas of personal life should apply to cryptocurrency. For one, diversification of storage approach and weighing of risks. Digital assets are no different, he says, when it comes to backing up personal and sensitive data on the cloud to ensure data against loss or corruption.

Companies including Coinbase and Jack Dorsey’s Block offer products that try to merge some of these ideas, creating a more secure version of a crypto wallet that remains convenient to use. There is Coinbase Vault, which includes enhanced security steps before a user can access crypto holdings for trading. And there is Coinbase Wallet and Block’s Bitkey, which have mobile apps that work like a traditional wallet making moving bitcoin around easy, but with the ability to pair with hardware wallets and added security more commonly associated with cold storage.

Bitkey hardware requires multiple authorizations for transactions for added security, similar to “multi-sig wallets.” Bitkey also offers recovery tools so one of the biggest risks of self-custody — losing codes or phrases needed to recover a cold wallet — is less of an issue.

Solutions like Dorsey’s may help to solve the tension between convenience and security; at minimum, they underline that this tension exists and will likely be something of a roadblock to more widespread crypto adoption. Beyond the risks out there in the form of wildfires, all kinds of natural disasters, and wars, bitcoin self-custody can be vulnerable to the biggest personal risk of all: unexpected death of the bitcoin owner. There is arguably nothing more complicated than inheritance when it comes to unlocking the crypto chain of custody.

Coinbase requires probate court documents and specific will designations before releasing funds from custody, while physical wallets offer little to no support, potentially leaving all that digital value stuck on a private key. Bitkey rolled out its inheritance solution in February for what a Bitkey executive called, “kind of a multibillion-dollar problem waiting to happen.”

“People who have a material investment in bitcoin absolutely need to be thinking differently about how to protect it,” Neuman said. He says that after disasters like the California wildfires, or when exchanges go bust like FTX, the industry does see more crypto holders taking action to move to more secure storage setups. “I suppose it’s human nature to wait until ‘bad things happen’ to spur action to improve your own personal situation,” he said. “But I think people would be better off if they were more proactive. Otherwise, they risk having that ‘bad thing’ happen to them, and then it’s too late,” he said.

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