Chicago’s Sprout Social prices IPO mid-range at $17 per share, raising $150M

On the heels of Bill.com’s debut, Chicago-based social media software company Sprout Social priced its IPO last night at $17 per share, in the middle of its proposed $16 to $18 per-share range. Selling 8.8 million shares, Sprout raised just under $150 million in its debut.

Underwriters have the option to purchase an additional 1.3 million shares if they so choose.

The IPO is a good result for the company’s investors (Lightbank, New Enterprise Associates, Goldman Sachs, and Future Fund), but also for Chicago, a growing startup scene that doesn’t often get its due in the public mind.

At $17 per share, not including the possible underwriter option, Sprout Social is worth about $814 million. That’s just a hair over its final private valuation set during its $40.5 million Series D in December of 2018. That particular investment valued Sprout at $800.5 million, according to Crunchbase data.

So what?

Sprout’s debut is interesting for a few reasons. First, the company raised just a little over $110 million while private, and will generate over $100 million in trailing GAAP revenue this year. In effect, Sprout Social used less than $110 million to build up over $100 million in annual recurring revenue (ARR) — the firm reached the $100 million ARR mark in between Q2 and Q3 of 2019. That’s a remarkably efficient result for the unicorn era.

And the company is interesting as it gives us a look at how investors value slower-growth SaaS companies. As we’ve written, Sprout Social grew by a little over 30% in the first three quarters of 2019. That’s a healthy rate, but not as fast as, say, Bill.com . (Bill.com’s strong market response puts its own growth rate in context.)

Thinking very loosely, Sprout Social closed Q3 2019 with ARR of about $105 million. Worth $814 million now, we can surmise that Sprout priced at an ARR multiple of about 7.75x. Thats a useful benchmark for private companies that sell software: if you want a higher multiple when you go public, you’ll have to grow a little faster.

All the same, the IPO is a win for Chicago, and a win for their number of investors. We’ll update this piece later with how the stock performs, once it begins to trade.


By Alex Wilhelm

GitLab hauls in $268M Series E on 2.768B valuation

GitLab is a company that doesn’t pull any punches or try to be coy. It actually has had a page on its website for sometime stating it intends to go public on November 18, 2020. You don’t see that level of transparency from late-stage startups all that often. Today, the company announced a huge $268 million Series E on a tidy $2.768 billion valuation.

Investors included Adage Capital Management, L.P, Alkeon Capital, Altimeter Capital, Blackrock, Inc., Capital Group, Coatue Management, D1 Capital Partners, Franklin Templeton, Light Street Capital, Tiger Management Corp and Two Sigma Investments LP.

The company seems to be primed and ready for that eventual IPO. Last year, GitLab co-founder and CEO Sid Sijbrandij says that his CFO Paul Machle told him he wanted to begin planning to go public, and he would need two years in advance to prepare the company. As Sijbrandij tells it, he told him to pick a date.

“He said, I’ll pick the 16th of November because that’s the birthday of my twins. It’s also the last week before Thanksgiving, and after Thanksgiving, the stock market is less active, so that’s a good time to go out,” Sijbrandij told TechCrunch.

He said that he considered it a done deal and put the date on the GitLab Strategy page, a page that outlines the company’s plans for everything it intends to do. It turned out that he was a bit too quick on the draw. Machle had checked the date in the interim and realized that it was a Monday, which is not traditionally a great day to go out, so they decided to do it two days later. Now the target date is officially November 18, 2020.

Screenshot 2019 09 17 08.35.33 2

GitLab has the date it’s planning to go public listed on its Strategy page.

As for that $268 million, it gives the company considerable runway ahead of that planned event, but Sijbrandij says it also gives him flexibility in how to take the company public. “One other consideration is that there are two options to go public. You can do an IPO or direct listing. We wanted to preserve the optionality of doing a direct listing next year. So if we do a direct listing, we’re not going to raise any additional money, and we wanted to make sure that this is this is enough in that case,” he explained.

Sijbrandij says that the company made a deliberate decision to be transparent early on. Being based on an open source project, it’s sometimes tricky to make that transition to commercial company, and sometimes that has a negative impact on the community and the number of contributions. Transparency was a way to combat that, and it seems to be working.

He reports that the community contributes 200 improvements to the GitLab open source product every month, and that’s double the amount of just a year ago, so the community is still highly active in spite of the parent company’s commercial success.

It did not escape his notice that Microsoft acquired GitHub last year for $7.5 billion. It’s worth noting that GitLab is a similar kind of kind of company that helps developers manage and distribute code in a DevOps environment. He claims in spite of that eye-popping number, his goal is to remain an independent company and take this through to the next phase.

“Our ambition is to stay an independent company. And that’s why we put out the ambition early to become a listed company. That’s not totally in our control as the majority of the company is owned by investors, but as long as we’re more positive about the future than the people around us, I think we can we have a shot at not getting acquired,” he said.

The company was founded in 2014 and was a member of Y Combinator in 2015. It has been on a steady growth trajectory ever since. hauling in over $436 million. The last round before today’s announcement was a $100 million Series D last September.


By Ron Miller

The Exit: The acquisition charting Salesforce’s future

Before Tableau was the $15.7 billion key to Salesforce’s problems, it was a couple of founders arguing with a couple of venture capitalists over lunch about why its Series A valuation should be higher than $12 million pre-money.

Salesforce has generally been one to signify corporate strategy shifts through their acquisitions, so you can understand why the entire tech industry took notice when the cloud CRM giant announced its priciest acquisition ever last month.

The deal to acquire the Seattle-based data visualization powerhouse Tableau was substantial enough that Salesforce CEO Marc Benioff publicly announced it was turning Seattle into its second HQ. Tableau’s acquisition doesn’t just mean big things for Salesforce. With the deal taking place just days after Google announced it was paying $2.6 billion for Looker, the acquisition showcases just how intense the cloud wars are getting for the enterprise tech companies out to win it all.

The Exit is a new series at TechCrunch. It’s an exit interview of sorts with a VC who was in the right place at the right time but made the right call on an investment that paid off. [Have feedback? Shoot me an email at [email protected]]

Scott Sandell, a general partner at NEA (New Enterprise Associates) who has now been at the firm for 25 years, was one of those investors arguing with two of Tableau’s co-founders, Chris Stolte and Christian Chabot. Desperate to close the 2004 deal over their lunch meeting, he went on to agree to the Tableau founders’ demands of a higher $20 million valuation, though Sandell tells me it still feels like he got a pretty good deal.

NEA went on to invest further in subsequent rounds and went on to hold over 38% of the company at the time of its IPO in 2013 according to public financial docs.

I had a long chat with Sandell, who also invested in Salesforce, about the importance of the Tableau deal, his rise from associate to general partner at NEA, who he sees as the biggest challenger to Salesforce, and why he thinks scooter companies are “the worst business in the known universe.”

The interview has been edited for length and clarity. 


Lucas Matney: You’ve been at this investing thing for quite a while, but taking a trip down memory lane, how did you get into VC in the first place? 

Scott Sandell: The way I got into venture capital is a little bit of a circuitous route. I had an opportunity to get into venture capital coming out of Stanford Business School in 1992, but it wasn’t quite the right fit. And so I had an interest, but I didn’t have the right opportunity.


By Lucas Matney

Under the hood on Zoom’s IPO, with founder and CEO Eric Yuan

Extra Crunch offers members the opportunity to tune into conference calls led and moderated by the TechCrunch writers you read every day. This week, TechCrunch’s Kate Clark sat down with Eric Yuan, the founder and CEO of video communications startup Zoom, to go behind the curtain on the company’s recent IPO process and its path to the public markets.

Since hitting the trading desks just a few weeks ago, Zoom stock is up over 30%. But the Zoom’s path to becoming a Silicon Valley and Wall Street darling was anything but easy. Eric tells Kate how the company’s early focus on profitability, which is now helping drive the stock’s strong performance out of the gate, actually made it difficult to get VC money early on, and the company’s consistent focus on user experience led to organic growth across different customer bases.

Eric: I experienced the year 2000 dot com crash and the 2008 financial crisis, and it almost wiped out the company. I only got seed money from my friends, and also one or two VCs like AME Cloud Ventures and Qualcomm Ventures.

nd all other institutional VCs had no interest to invest in us. I was very paranoid and always thought “wow, we are not going to survive next week because we cannot raise the capital. And on the way, I thought we have to look into our own destiny. We wanted to be cash flow positive. We wanted to be profitable.

nd so by doing that, people thought I wasn’t as wise, because we’d probably be sacrificing growth, right? And a lot of other companies, they did very well and were not profitable because they focused on growth. And in the future they could be very, very profitable.

Eric and Kate also dive deeper into Zoom’s founding and Eric’s initial decision to leave WebEx to work on a better video communication solution. Eric also offers his take on what the future of video conferencing may look like in the next five to 10 years and gives advice to founders looking to build the next great company.

For access to the full transcription and the call audio, and for the opportunity to participate in future conference calls, become a member of Extra Crunch. Learn more and try it for free. 

Kate Clark: Well thanks for joining us Eric.

Eric Yuan: No problem, no problem.

Kate: Super excited to chat about Zoom’s historic IPO. Before we jump into questions, I’m just going to review some of the key events leading up to the IPO, just to give some context to any of the listeners on the call.


By Arman Tabatabai

Canonical plans to raise its first outside funding as it looks to a future IPO

It’s been 14 years since Mark Shuttleworth first founded and funded Canonical and the Ubuntu project. At the time, it was mostly a Linux distribution. Today, it’s a major enterprise player that offers a variety of products and services. Throughout the years, Shuttleworth self-funded the project and never showed much interest in taking outside money. Now, however, that’s changing.

As Shuttleworth told me, he’s now looking for investors as he looks to get the company on track to an IPO. It’s no secret that the company’s recent re-focusing on the enterprise — and shutting down projects like the Ubuntu phone and the Unity desktop environment — was all about that, after all. Shuttleworth sees raising money as a step in this direction — and as a way of getting the company in shape for going public.

“The first step would be private equity,” he told me. “And really, that’s because having outside investors with outside members of the board essentially starts to get you to have to report and be part of that program. I’ve got a set of things that I think we need to get right. That’s what we’re working towards now. Then there’s a set of things that private investors are looking for and the next set of things is when you’re doing a public offering, there’s a different level of discipline required.”

It’s no secret that Shuttleworth, who sports an impressive beard these days, was previously resistant to this, and he acknowledged as much. “I think that’s a fair characterization,” he said. “I enjoy my independence and I enjoy being able to make long-term calls. I still feel like I’ll have the ability to do that, but I do appreciate keenly the responsibility of taking other people’s money. When it’s your money, it’s slightly different.”

Refocusing Canonical on the enterprise business seems to be paying off already. “The numbers are looking good. The business is looking healthy. It’s not a charity. It’s not philanthropy,” he said. “There are some key metrics that I’m watching, which are the gate for me to take the next step, which would be growth equity.” Those metrics, he told me, are the size of the business and how diversified it is.

Shuttleworth likens this program of getting the company ready to IPO to getting fit. “There’s no point in saying: I haven’t done any exercise in the last 10 years but I’m going to sign up for tomorrow’s marathon,” he said.

The move from being a private company to taking outside investment and going public — especially after all these years of being self-funded — is treacherous, though, and Shuttleworth admitted as much, especially in terms of being forced to setting short-term goals to satisfy investors that aren’t necessarily in the best interest of the company in the long term. Shuttleworth thinks he can negotiate those issues, though.

Interestingly, he thinks the real danger is quite a different one. “I think the most dangerous thing in making that shift is the kind of shallowness of the unreasonably big impact that stock price has on people’s mood,” he said. “Today, at Canonical, it’s 600 people. You might have some that are having a really great day and some that are having a shitty day. And they have to figure out what’s real about both of those scenarios. But they can kind of support each other. […] But when you have a stock ticker, everybody thinks they’re having a great day, or everybody thinks they’re having a shitty day in a way that may be completely uncorrelated to how well they’re actually doing.”

Shuttleworth does not believe that IBM’s acquisition of its competitor Red Hat will have any immediate effect on its business, though. What he does think, however, is that this move is making a lot of people rethink for the first time in years the investment they’ve been making in Red Hat and its enterprise Linux distribution. Canonical’s promise is that Ubuntu, as well as its OpenStack tools and services, are not just competitive but also more cost-effective in the long run, and offer enterprises an added degree of agility. And if more businesses start looking at Canonical and Ubuntu, that can only speed up Shuttleworth’s (and his bankers’) schedule for hitting Canonical’s metrics for raising money and going public.


By Frederic Lardinois

Pluralsight prices its IPO at $15 per share, raising over $300M

Pluralsight priced the shares in its IPO at $15 this afternoon, above its previously set target range of between $12 and $14, and will raise as much as $357 million ahead of its public debut tomorrow morning.

Pluralsight offers software development courses, specifically ones targeting employees that are looking to advance in their careers by acquiring new skills in order to transition to higher-level roles. As knowledge workers become increasingly valuable, especially in larger enterprises with sprawling workforces, companies like Pluralsight have found a sweet spot in building tools that enable companies to help identify talent in their own workforce and train them, rather than have to aggressively search outside the company to satisfy their needs. The company has raised $310.5 million in its IPO, with underwriters having the option to purchase an additional 3.1 million shares and bring that up to $357 million.

The company is one of a continuing wave of enterprise IPOs this year, including multiple successful ones like zScalar and Dropbox — the latter of which was more of a flagship as both a hotly-anticipated one and as a company that possesses a unique business model. But nonetheless, it’s shown that there’s an appetite for enterprise startups looking to go public, which offers those companies a way to raise capital in addition to offering their employees liquidity.

Pluralsight will be another of an increasing pack of unicorns in the Utah tech scene that are on their way to going public. Founded in 2004, Pluralsight was largely bootstrapped until its first financing round in 2013 where it raised $27.5 million from Insight Venture Partners. That firm is the company’s largest shareholder, and since then Pluralsight has raised nearly $200 million in financing.

Its The company’s IPO tomorrow will once again test the appetite for fresh IPOs among public investors. Enterprise companies generally offer a more stable batch for venture portfolios, with predictable and reliable growth that eventually carries it to an IPO with varying levels of success. They’re smaller than blockbuster consumer-ish IPOs, but they are the ones that can provide a stable return for funds like IVP.


By Matthew Lynley

DocuSign pops 30% and Smartsheet 23% in their debuts on Nasdaq and NYSE

Enterprise tech IPOs continue to roar in 2018. Today, not one but two enterprise tech companies, DocuSign and Smartsheet, saw their share prices pop as they made their debuts on to the public markets.

As of 12:53 New York time, DocuSign is trading higher at $39.39, up 36 percent from its IPO price and giving the company a market cap of $6 billion. Smartsheet is at $18.55, giving it a market cap of $1.8 billion. We’ll continue to update these numbers during the day.

Smartsheet was first out of the gates. Trading on NYSE under the ticker SMAR, the company clocked an opening price of $18.40. This represented a pop of 22.7 percent on its IPO pricing of $15 yesterday evening — itself a higher figure than the expected range of $12-$14. The company, whose primary product is a workplace collaboration and project management platform (it competes with the likes of Basecamp, Wrike and Asana), raised $150 million in its IPO and is currently trading around $18.30/share.

Later in the day, DocuSign — a company that facilitates e-signatures and other features to speed up contractural negotiations online, competing against the likes of AdobeSign and HelloSign — also started to trade, and it saw an even bigger pop. Trading on Nasdaq under DOCU, the stock opened at $37.75, which worked out to a jump of 30 percent on its IPO price last night of $29. Like Smartsheet, DocuSign had priced its IPO higher than the expected range of $26-$28, raising $629 million in the process.

In the case of both companies, they are coming to the market with net losses on their balance sheets, but evidence of strong revenue growth. And in a period that seems to be a generally strong market for IPOs at the moment, combined with the generally positive climate for cloud-based enterprise services (with both Microsoft and Amazon crediting their cloud businesses for their own strong earnings), that rising tide appears to be lifting these two boats.

DocuSign reported $518.5 million in revenue for its fiscal year ending in 2018 in its IPO filings, up from $381.5 million last year and $250.5 million in 2016. Losses were $52.3 million, but that figure was halved over 2017, when it posted a net loss of $115.4 million. DocuSign’s customers include T-Mobile, Salesforce, Morgan Stanley and Bank of America.

Smartsheet reported 3.6 million users in its IPO filings, with business customers including Cisco and Starbucks. The company brought in $111.3 million in revenue for its fiscal 2018 year, but as with many SaaS companies, it’s going public with a loss. Specifically in 2018 it reported a loss of $49.1 million for 2018, up from a net loss of $15.2 million and $14.3 million in 2017 and 2016 respectively.

Other strong enterprise tech public offerings this year have included Dropbox, Zscaler, Cardlytics, Zuora and Pivotal. All of them closed above their opening prices, in what is shaping up to be a huge year for tech IPOs overall.

We’ll update the pricing as the day progresses.


By Ingrid Lunden

Pivotal Software closed up 5% following IPO, raised $555 million

Stock market investors showed lukewarm enthusiasm for Pivotal Software’s debut on Friday. After pricing the IPO at $15, the company closed the day at $15.73.

Although it didn’t “pop” for new investors, pricing at the midpoint of its proposed range allowed Pivotal to raise $555 million. Its public company market cap exceeded $3 billion.

The enterprise cloud computing company has been majority-owned by Dell, which came about after its merger with EMC in 2016. It was spun off from Dell, EMC and VMware in April 2013.

After that, it raised $1.7 billion in funding from Microsoft, Ford and General Electric.

Here’s how it describes its business in the S-1 filing:

Pivotal looks to “provide a leading cloud-native platform that makes software development and IT operations a strategic advantage for our customers. Our cloud-native platform, Pivotal  Cloud Foundry (‘PCF’), accelerates and streamlines software development by reducing the complexity of building, deploying and operating new cloud-native applications and modernizing legacy applications.”

According to the filing, Pivotal brought in $509.4 million in revenue for its fiscal year ending in February. This is up from $416.3 million in revenue for 2017 and $280.9 million in revenue the year before.

The company is still losing a lot of money, however. Losses for fiscal 2018 stood at $163.5 million, improved from the than the negative $232.5 million seen in 2017 and $282.5 million in 2016.

“We have incurred substantial losses and may not be able to generate sufficient revenue to achieve and sustain profitability,” the company warned in the requisite “risk factors” section of its IPO filing.

Pivotal also acknowledged that it faces competition from “legacy application infrastructure and middleware form vendors” like IBM and Oracle. The company says it additionally competes with “open-source based offerings supported by vendors” like RedHat. Pivotal also faces challenges from SAP Cloud Platform, Amazon Web Services and Microsoft Azure.

The company says it believes it will stand out from the pack because of its strong security and easy-to-use platform. Pivotal also claims to have strong brand awareness and a good reputation. It has 118 U.S. patents and 73 pending and is betting that it will remain innovative.

Morgan Stanley and Goldman Sachs served as lead underwriters. Davis Polk and Fenwick & West worked as counsel.

The company listed on the New York Stock Exchange under the ticker “PVTL.”

It has been an active spring for tech IPOs, after a slow winter. Dropbox, Spotify and Zuora are amongst the companies that have gone public in recent weeks. DocuSign, Smartsheet, Carbon Black and Pluralsight are all expected to debut within the next month.

Subscription biller Zuora soars 43% following IPO

Subscription biller Zuora was well-received by stock market investors on Thursday, following its public debut. After pricing its IPO at $14, the company closed at $20, valuing the company around $2 billion.

It was also much higher than expected. The company said in its filings that it planned to price its shares between $9 and $11, before it raised that range to $11 to $13.

Founder and CEO Tien Tzuo told TechCrunch that he believes “a bet on us is really a bet on an entire shift to a new business model, to a subscription economy.” He is optimistic that subscriptions are the “business model of the future.”

Zuora sees itself as an early pioneer in a growing category. The company believes that more businesses will shift their business models to subscriptions, across sectors like media and entertainment, transportation, publishing, industrial goods and retail.

It helps its 950 customers manage subscriptions, including billing and revenue recognition. Zuora touts that it has 15 of the Fortune 100 businesses as clients.

Zuora’s revenue for its fiscal 2018 year was $167.9 million. This was up from $113 million in 2017 and $92.2 million the year before. Losses remained constant in this timeframe, from $48.2 million in 2016 to $47.2 million in 2018.

“We have a history of net losses, anticipate increasing our operating expenses in the future, and may not achieve or sustain profitability,” warned the requisite risk factors section of the filing.

It also acknowledged a competitive landscape. Oracle and SAP are amongst the companies offering software in the ERP (enterprise resource planning) category. It also competes with other startups like Chargebee.

The largest shareholders are Benchmark, which owned 11.1% prior to the IPO . Founder and CEO Tien Tzuo owned 10.2%. Others with a significant stake included Wellington Management, Shasta Ventures, Tenaya Capital and Redpoint.

The San Mateo, California-based company previously raised over $240 million, dating back to 2007.

Zuora listed on the New York Stock Exchange, under the ticker “ZUO.” Goldman Sachs and Morgan Stanley worked as lead underwriters on the deal. Fenwick & West and Wilson Sonsini served as counsel.

After a slow start to the year for tech IPOs, there has been a flurry of activity in recent weeks. Dropbox and Spotify were amongst the recent public debuts. We also have DocuSign, Pivotal and Smartsheet on the horizon.

Dropbox finishes up 36% on first day of trading

Dropbox was off to the races on its first day as a public company.

After pricing above the range at $21 per share, raising $756 million, Dropbox kicked off its first day soaring to $31.60, and closing the day at $28.48. This is up almost 36%.

It’s surely a sign of public investor enthusiasm for the cloud storage business, which had initially hoped to price its IPO between $16 and $18 and then raised it from $18 to $20.

It also means that Dropbox closed well above the $10 billion it was valued at its last private round. Its market cap is now above $12 billion, fully diluted.

Dropbox brought in $1.1 billion in revenue for the last year. This compares to $845 million in revenue the year before and $604 million for 2015.

While it’s been cash flow positive since 2016, it is not yet profitable, having lost nearly $112 million last year. But it is significantly improved margins when compared to losses of $210 million for 2016 and $326 million for 2015.

Its average revenue per paying user is $111.91.

There has been a debate about whether to value Dropbox, which has a freemium model, as a consumer company or an enterprise business. It has convinced just 11 million of its 500 million registered customers to pay for its services.

Dropbox “combines the scale and virality of a consumer company with the recurring revenue of a software company,” said Bryan Schreier, a general partner at Sequoia Capital and board member at the company. He said that now was the time for Dropbox to list because “the business had reached a level of scale and also cash flow that warranted a public debut.”

He also talked about the early days of Dropbox pitching at a TechCrunch event in 2008 and how disappointed they were that the slides stopped working during the presentation. We have footage of that here.

Sequoia Capital owned 23.2% of the overall shares outstanding at the time of the IPO. They shared Dropbox’s original seed pitch from 2007. 

Accel was the next largest shareholder, owning 5% overall. Sameer Gandhi made the investment at Sequoia and then invested in Dropbox again when he went over to Accel.

Founder and CEO Drew Houston owned 25.3% of the company.

Greylock Partners also had a small stake. John Lilly, a general partner there, said he “invested in Dropbox because Drew and the team had an exceptionally clear vision of what the future of work would look like and built a product that would that meet the demands of the modern workforce.”

But there are quite a few other businesses with similar products to Dropbox. The prospectus warned of the competitive landscape.

“The market for content collaboration platforms is competitive and rapidly changing. Certain features of our platform compete in the cloud storage market with products offered by Amazon, Apple, Google, and Microsoft, and in the content collaboration market with products offered by Atlassian, Google, and Microsoft. We compete with Box on a more limited basis in the cloud storage market for deployments by large enterprises.”

Note that it downplayed its competition with Box, a company that’s often mentioned in the same sentence as Dropbox. While the products are similar, the two have different business models and Dropbox was hoping that this would be respected with a better revenue multiple. If the first day is any indication, it looks like that strategy worked.

The company listed on the Nasdaq, under the ticker “DBX.”

We talked about Dropbox’s first day and the outlook for upcoming public debuts like Spotify on our “Equity” podcast episode below. We were joined by Eric Kim, managing partner at Goodwater Capital.  He authored a research report here. 

Dropbox finishes up 36% on first day of trading, valuing company above $11 billion

Dropbox was off to the races on its first day as a public company.

After pricing above the range at $21 per share, raising $756 million, Dropbox kicked off its first day soaring to $31.60, and closing the day at $28.48. This is up almost 36%.

It’s surely a sign of public investor enthusiasm for the cloud storage business, which had initially hoped to price its IPO between $16 and $18 and then raised it from $18 to $20.

It also means that Dropbox closed well above the $10 billion it was valued at its last private round. Its market cap is about $11.1 billion.

Dropbox brought in $1.1 billion in revenue for the last year. This compares to $845 million in revenue the year before and $604 million for 2015.

While it’s been cash flow positive since 2016, it is not yet profitable, having lost nearly $112 million last year. But it is significantly improved margins when compared to losses of $210 million for 2016 and $326 million for 2015.

Its average revenue per paying user is $111.91.

There has been a debate about whether to value Dropbox, which has a freemium model, as a consumer company or an enterprise business. It has convinced just 11 million of its 500 million registered customers to pay for its services.

Dropbox “combines the scale and virality of a consumer company with the recurring revenue of a software company,” said Bryan Schreier, a general partner at Sequoia Capital and board member at the company. He said that now was the time for Dropbox to list because “the business had reached a level of scale and also cash flow that warranted a public debut.”

He also talked about the early days of Dropbox pitching at a TechCrunch event in 2008 and how disappointed they were that the slides stopped working during the presentation. The company has come a long way.

Sequoia Capital owned 23.2% of the overall shares outstanding at the time of the IPO. They shared Dropbox’s original seed pitch from 2007. 

Accel was the next largest shareholder, owning 5% overall. Sameer Gandhi made the investment at Sequoia and then invested in Dropbox again when he went over to Accel.

Founder and CEO Drew Houston owned 25.3% of the company.

Greylock Partners also had a small stake. John Lilly, a general partner there, said he “invested in Dropbox because Drew and the team had an exceptionally clear vision of what the future of work would look like and built a product that would that meet the demands of the modern workforce.”

The prospectus warned of the competitive landscape.

“The market for content collaboration platforms is competitive and rapidly changing. Certain features of our platform compete in the cloud storage market with products offered by Amazon, Apple, Google, and Microsoft, and in the content collaboration market with products offered by Atlassian, Google, and Microsoft. We compete with Box on a more limited basis in the cloud storage market for deployments by large enterprises.”

Note that they downplayed their competition with Box, a company that’s often mentioned in the same sentence as Dropbox. While the products are similar, the two have different business models and Dropbox was hoping that this would be respected with a better revenue multiple. If the first day is any indication, it looks like that strategy worked.

The company listed on the Nasdaq, under the ticker “DBX.”

We talked about Dropbox’s first day and the outlook for upcoming public debuts like Spotify on our “Equity” podcast episode below. We were joined by Eric Kim at Goodwater Capital.

Y Combinator’s Jessica Livingston on Dropbox IPO: “It was just a dream of ours”

Dropbox, after more than a decade, finally went public this morning — and the stock soared more than 40% in its initial trading, making it a marquee success for one of the original Web 2.0 companies (at least for now).

While we still have to wait for the dust to settle, it’s been a very long road for Dropbox. From starting off as a file-sharing service, to hitting a $10 billion valuation in the middle of a massive hype cycle, to expectations dropping and then the announcement of a $1 billion revenue run rate. Dropbox has been a rollercoaster, but it’s another big moment this afternoon: it’s Y Combinator’s first big IPO. And Y Combinator still has a very deep bench of startups that are, thus far, obvious IPO candidates down the line like Airbnb and Stripe.

That isn’t to take away anything from the work of CEO Drew Houston and the rest of Dropbox’s team, but Y Combinator’s job is to basically take a bunch of shots in the dark based on good ideas and potentially savvy founders. Houston was one of the first of a firm that now takes in a hundred-odd founders per class. Y Combinator Founder and partner Jessica Livingston was there for the start of it, recalling back to the day that Houston rushed to her and Paul Graham to show him his little side project.

We caught up with Livingston this morning ahead of the IPO for a short interview. Here’s the conversation, which was lightly edited for clarity:

TC: Can you tell us a little bit about what it’s like to finally see the first Y Combinator company to go public?

JL: I feel like 13 years ago, it was just this dream of ours. It was this seemingly unattainable dream that goes, ‘maybe one of the startups we fund could go public someday.’ That was the holy grail. It’s an exciting day for Y Combinator. It shows what a long game investing is in early-stage startups. I do feel kind of validated.

TC: How did Y Combinator first end up in touch with Houston?

JL: He applied as a solo founder. We had met Drew the summer before. Back then, we were so small that we always encouraged people to bring friends to a Y Combinator dinner. [Xobni founder Adam Smith] brought [Houston], and we met him then and talked it through. When he applied, we invited him to come to an interview, and Paul [Graham] before the interview reached out to [Houston]. He said, “I see you’re a solo founder, and you should find a cofounder.” Three weeks later Drew showed up with [co-founder Arash Ferdowsi]. It was a great match that worked well.

TC: As Dropbox has grown, what’s stood out to you the most during changes in the market?

JL: They’re a classic example of founders who are programmers who built something to solve their own problem. Clearly, this is a perfect example of that. Drew gets on the bus, he forgets his files, and he can’t work on the whole trip down. He then creates something that will allow him to access files from everywhere. At the time, when he came on the scene with that, there were a lot of companies doing it but none were very good. I feel like Dropbox, regardless of market dynamics, from the very beginning was always dedicated to wanting to do well by building a better solution. They wanted to build one that actually works. I feel like they’ve stuck to that and that’s been driving them since. That’s been their guidepost.

TC: What was your first meeting with Houston like, and do you think he has changed in the past 10 years?

JL: When I first met him, he was young — he was very young — and he was always a good hacker, and very earnest. During Y Combinator he was very focused on building this product and was not distracted by other things. That’s when there were just two people. He’s really evolved over the years as an incredible leader. He’s grown this company and he’s navigated through all different parts of his life cycle. I’ve witnessed his growth as a leader and as a human being. He’s always been a great person. It’s sort of exciting to see where he is now that he’s come a long way, it’s really cool.

TC: Houston and Ferdowsi still own significant portions of the company even after raising a lot of venture capital. Do you think Y Combinator had any effect on companies looking for more founder friendly deals?

JL: I think when Y Combinator started, our goal in many ways was to empower founders. It was to level the playing field. You don’t have to have a connection in Silicon Valley to get funding. You just have to apply on our website. You don’t have to have gone to an Ivy League school. We [try to tell them], don’t let investors take advantage of you because you’re young and have never done this before. In general, times have changed over the past 15 years. Hopefully Y Combinator played a small role in some of those changes in making things a little more found friendly.

TC: What’s one of your favorite stories about Houston?

JL: He was always very calm, cool, and collected under pressure. I remember that was definitely a quality about him. His feathers didn’t get ruffled easily. One of the things I remember most clearly is from that summer when we had demo day. Back then it was, like, 40 people tops. Still, there was a lot of pressure. I remember Paul [Graham] came up with this idea that, ‘hey, Drew, during your demo day you should show people how well Dropbox actually works by deleting your presentation live and restoring it through Dropbox.’ That’s kind of risky, right? To delete your presentation. You’re just standing up there without anything. And he did it and he nailed the presentation. It sounds a little gimmicky, but it really worked and showed his product worked. I remember thinking, like, wow, he’s pretty calm. If it were me I don’t think I could hit the delete button in front of these people. That’s an important quality in someone, not to get flustered.

By the way, we funded them in 2007. If you asked me in 2008 how were they doing, I would say, well, they’re making progress. But it wasn’t like we funded them and we could say, ‘this is gonna be a great one.’ We just knew, yeah they’re making progress, but it’s always hard to know there.

TC: Back then, what were you just expecting? M&A? Did you even anticipate an IPO?

JL:  As we were formulating the idea, the hope was rather than going to work at Microsoft — I use them as an example because that was the company back then — and rather than going to get a job out of college, why not build a company and make Microsoft acquire you to get you to work for them? We had low expectations back then. We were hoping there’d be some small acquisitions. But yes, the hope was always acquisitions, but maybe someday in our wildest dreams there’d be an IPO. We didn’t even think YC would work when we started, people didn’t believe in YC’s models for many years.

TC: Looking back, what would you say is one of the biggest things you’ve learned throughout this experience?

JL: What a long road it is for startups. When we started YC back then, it wasn’t a popular thing to do a startup. Now, thank goodness, more people are starting them, and more types of people are starting them. It’s not just super high-tech companies. That’s exciting, but what I think a lot of people don’t realize is how hard startups are. You say, yeah, I know how hard, but people don’t realize how difficult they are and how long the commitment is. If you’re successful, it takes such a long time. For [someone like Houston] to make it to that point, they’ve committed a lot of their life and energy and all their intellectual capacity to making this work. To me, that’s so exciting, but I think it would surprise people to know realistically how long that could take.

TC: What would you tell startups with the hindsight of what happened with Dropbox’s valuation hype cycle?

JL: I will say, with startups, sometimes you just have to stick to what you’re doing. There’s a lot of stuff going on around you, especially now with social media and things like that. With a startup, you just have to keep moving forward with building a company and building a great product.

DocuSign has filed confidentially for IPO

DocuSign is gearing up to go public in the next six months, sources tell TechCrunch.

The company, which pioneered the e-signature has been talking about an IPO for a while but has now filed confidentially, we are hearing.

Like Dropbox, which is finally going public this week, San Francisco-based DocuSign has been an anticipated IPO for several years now. It’s raised over $500 million since it was founded in 2003 and has been valued at $3 billion. Kleiner Perkins, Bain Capital, Intel Capital, GV (Google Ventures) and Dell are amongst the many well-known names which have invested in DocuSign.

But like many “unicorns” these days, the company took its time, spending 15 years as a private company. The DocuSign team decided that 2018 is the year that it is finally ready and is targeting an IPO in either the second or third quarter.

San Francisco-based DocuSign, which competes with HelloSign and Adobe Sign, amongst others, has been on a mission to get the world’s businesses to sign documents online. The team has worked with large enterprises like T-Mobile, Salesforce, Morgan Stanley and Bank of America.

The company has a tiered business model, with corporations paying more for added services. Public investors will be evaluating DocuSign both on its revenue growth and customer retention.

North America is their largest market, but they’ve been focused on expanding throughout the world, including the U.K., France, Australia, Brazil, Singapore and Japan.

Since its inception, DocuSign has undergone several management changes. Early last year, Dan Springer took the helm. He was formerly CEO of Responsys, which went public and then was bought by Oracle for $1.5 billion.

Keith Krach, who is now chairman, had been running the company since 2011. Krach was previously CEO of Ariba, which was acquired by SAP for $4.3 billion.