Spotify
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When starting a tech company, there seems to be a playbook that most entrepreneurs follow. While some may start with a bit of bootstrapping, most will dive straight into raising seed money through investors. In many cases, this is a great path. It’s a path I’ve taken twice myself, first with GroupMe, and then again with Fundera.
Ironically, though, my second venture-backed company is a business focused on helping entrepreneurs find debt financing—a process I’ve gone through only once myself. But after five years of building and scaling this business, it’s made me take a step back and consider the question of when and where debt financing might be a better option for a business than equity financing, and vice versa.
I view these financing vehicles differently now than I did half a decade ago, and think it’s time we start to think a bit wider and diversely about how we finance our growing endeavors.
After all, when entrepreneurs take venture capital, they usually sign up to provide a 10x return on an investor’s capital. This expectation ultimately influences how they operate their business in the short-term. Maybe they’re not always ready for that expectation.
Or maybe they know they need to focus on building a good business before a great one. In this case, debt may be the better vehicle, where the only expectation is to pay it back.
Whether it’s money to get your business off the ground, capital to fuel additional growth, or cash to cover a gap, and whether you’re guiding the growth of a burgeoning startup, a smaller business, or even consulting firm helping other entrepreneurs, you should think critically about how you finance your business.
Here’s what to consider.
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Want to rock out together even when you’re apart? Spotify has prototyped an unreleased feature called “Social Listening” that lets multiple people add songs to a queue they can all listen to. You just all scan one friend’s QR-style Spotify Social Listening code, and then anyone can add songs to the real-time playlist. Spotify could potentially expand the feature to synchronize playback so you’d actually hear the same notes at the same time, but for now it’s a just a shared queue.
Social Listening could give Spotify a new viral growth channel, as users could urge friends to download the app to sync up. The intimate experience of co-listening might lead to longer sessions with Spotify, boosting ad plays or subscription retention. Plus, it could differentiate Spotify from Apple Music, YouTube Music, Tidal and other competing streaming services.

A Spotify spokesperson tells TechCrunch that “We’re always testing new products and experiences, but have no further news to share at this time.” Spotify already offers Collaborative Playlists friends can add to, but Social Listening is designed for real-time sharing. The company refused to provide further details on the prototype or when it might launch.
The feature is reminiscent of Turntable.fm, a 2011 startup that let people DJ in virtual rooms on their desktop that other people could join where they could chat, vote on the next song and watch everyone’s avatars dance. But the company struggled to properly monetize through ad-free subscriptions and shut down in 2014. Facebook briefly offered its own version called “Listen With…” in 2012 that let Spotify or Rdio users synchronize music playback.
Spotify Social Listening was first spotted by reverse-engineering sorceress and frequent TechCrunch tipster Jane Manchun Wong. She discovered code for the feature buried in Spotify’s Android app, but for now it’s only available to Spotify employees. Social Listening appears in the menu of connected devices you can open while playing a song beside nearby Wi-Fi and Bluetooth devices. “Connect with friends: Your friends can add tracks by scanning this code – You can also scan a friend’s code,” the feature explains.
A help screen describes Social Listening as “Listen to music together. 1. On your phone, play a song and select (Connected Devices). You’ll see a code at the bottom of the screen. 2. On your friend’s phone, select the same (Connected Devices) icon, tap SCAN CODE, and point the camera at your code. 3. Now you can control the music together.” You’ll then see friends who are part of your Social Listening session listed in the Connected Devices menu. Users can also copy and share a link to join their Social Listening session that starts with the URL prefix https://open.spotify.com/socialsession/. Note that Spotify never explicitly says that playback will be synchronized.

With streaming apps largely having the same music catalog and similar $9.99 per month premium pricing, they have to compete on discovery and user experience. Spotify has long been in the lead here with its algorithmically personalized Discover Weekly playlists, which were promptly copied by Apple and SoundCloud.
Oddly, Spotify has stripped out some of its own social features over the years, eliminating the in-app messaging inbox and instead pushing users to share songs over third-party messaging apps. The deemphasis in discovery through friends conveniently puts the focus on Spotify’s owned playlists. That gives it leverage over the record labels during their rate negotiations as it’s who influences which songs will become hits, so if labels don’t play nice their artists might not get promoted via playlists.
That’s why it’s good to see Spotify remembering that music is an inherently social experience. Music physically touches us through its vibrations, and when people listen to the same songs and are literally moved by it at the same time, it creates a sense of togetherness we’re too often deprived of on the internet.
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Most of the buzz about esports focuses on high-profile professional teams and audiences watching live streams of those professionals.
What gets ignored is the entire base of amateurs wanting to compete in esports below the professional tier. This is like talking about the NBA and the value of its sponsorships and broadcast rights as if that is the entirety of the basketball market in the US.
Los Angeles-based PlayVS (pronounced “play versus”) wants to become the dominant platform for amateur esports, starting at the high school level. The company raised $46 million last year—its first year operating—with the vision that owning the infrastructure for competitions and expanding it to encompass other social elements of gaming can make it the largest gaming company in the world.
I recently sat down with Founder & CEO Delane Parnell to talk about his company’s formation and growth strategy. Below is the transcript of our conversation (edited for length and clarity):

Eric P: You have a fascinating background as a serial entrepreneur while you were a teenager.
Delane P.: I grew up on the west side of Detroit and started working at the cell phone store of a family friend when I was 13. When I turned 16 or so, I joined two guys in opening our own Metro PCS franchise. And then two additional franchises. And I was on the founding team of a car rental company called Executive Rental Car.
Eric P: And this segued into tech startups after meeting Jon Triest from Ludlow Ventures?
Delane P: He got me a ticket to the Launch conference in SF, and that experience inspired me to start a Fireside Chat series in Detroit that brought in people like Brian Wong from Kiip and Alexis Ohanian from Reddit to speak. Starting at 21, I worked at a venture capital firm called IncWell based in Birmingham, Michigan then joined a startup called Rocket Fiber.
We were focused on internet infrastructure – this is 2015-ish – and I was appointed to lead our strategy in esports. So I met with many of the publishers, ancillary startups, tournament organizers, and OG players and team owners. Through the process, I became passionate about esports and ended up leaving Rocket Fiber to start a Call of Duty team that I quickly sold to TSM.
Eric P: What then drove you to found PlayVS? Did it seem like an obvious opportunity or did it take you a while to figure it out?
Delane P.: What esports means is playing video games competitively bound to governance and a competitive ruleset. As a player, what that experience means is you play on a team, in a position, with a coach, in a season that culminates in some sort of championship.
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Amazon and Walmart’s problems in India look set to continue after Narendra Modi, the biggest force to embrace the country’s politics in decades, led his Hindu nationalist Bharatiya Janata Party to a historic landslide re-election on Thursday, reaffirming his popularity in the eyes of the world’s largest democracy.
The re-election, which gives Modi’s government another five years in power, will in many ways chart the path of India’s burgeoning startup ecosystem, as well as the local play of Silicon Valley companies that have grown increasingly wary of recent policy changes.
At stake is also the future of India’s internet, the second largest in the world. With more than 550 million internet users, the nation has emerged as one of the last great growth markets for Silicon Valley companies. Google, Facebook, and Amazon count India as one of their largest and fastest growing markets. And until late 2016, they enjoyed great dynamics with the Indian government.
But in recent years, New Delhi has ordered more internet shutdowns than ever before and puzzled many over crackdowns on sometimes legitimate websites. To top that, the government recently proposed a law that would require any intermediary — telecom operators, messaging apps, and social media services among others — with more than 5 million users to introduce a number of changes to how they operate in the nation. More on this shortly.
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Does the overcrowded and cut-throat music streaming business have room for an additional player? The world’s most valuable startup certainly thinks so.
Chinese conglomerate ByteDance, valued at more than $75 billion, is working on a music streaming service, two sources familiar with the matter told TechCrunch. The company, which operates popular app TikTok, has held discussions with music labels in recent months to launch the app as soon as the end of this quarter, one of the sources said.
The app will offer both a premium and an ad-supported free tier, one of the sources said. Bloomberg, which first wrote about the premium app, reported that ByteDance is targeting emerging markets with its new music app. A ByteDance spokesperson declined to comment.
For ByteDance, interest in a music app does not come as a surprise. Snippets of pop songs from movies and albums intertwined with videos shot by its humongous user base is part of the service’s charm. The company already works with music labels worldwide to licence usage of their tracks on its platform. In China, where ByteDance claims to have tie-ups with more than 800 labels, it has been aggressively expanding efforts to find music talents and urge them to make their own tracks.
Besides, ByteDance has been expanding its app portfolio in recent months. Earlier this year, the company released Duoshan, a video chat app that appears to be a mix of TikTok and Snap. This week, it launched Feiliao, another chat app that is largely focused on text-driven conversations. At some point, the company may have realized the need for a standalone music consumption app.
When asked about TikTok’s partnership with music labels last month, Todd Schefflin, TikTok’s head of global music business development, told WSJ that music is part of the app’s “creative DNA” but it is “ultimately for short video creation and viewing, not a product for music consumption.”
The private Chinese company is likely eyeing India as a key market for its music app. The company has been in discussion with local music labels T Series and Times Music for rights. Moreover, its apps are estimated to have more than 300 million monthly active users in the nation, though there could be significant overlaps among them.
India may have also inspired ByteDance to consider a free, ad-supported version of its music app. Even as more than 150 million users in India listen to music online, only a tiny portion of this user base is willing to pay for it.
This has made India a unique battleground for local and international music giants, most of which offer an ad-supported, free version of their apps in the market. Even premium offerings from Apple and Spotify cost less than $1.2 a month. India is the only market where Spotify offers a free version of its app that has access to the entire catalog on demand.
The launch of the app could put the spotlight again on ByteDance in India, where its TikTok app recently landed in hot water. An Indian court banned the app for roughly a week after expressing concerns over questionable content on the platform. Ever since the nation lifted the ban on TikTok, the company has become visibly cautious about its movement.
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Spotify is testing its own version of Stories — the sharing format popularized by social apps like Snapchat and Instagram that has since made its way to other apps like Facebook, YouTube, WhatsApp and others. In Spotify’s case, it’s not called “Stories” but rather “Storyline,” and the focus is on allowing artists to share their own insights, inspiration, details about their creative process or other meanings behind the music.
This is very much similar to what Spotify’s “Behind the Lyrics” feature today offers. But instead of pop-up cards that load in time with the music, Spotify Storyline is very much a Stories-like experience, where users tap through the different screens at their own pace, and where horizontal lines at the top indicate how many screens still await them ahead.
@spotify hi. for about a yr now my band’s mgmt has tried get yall to take down some… outdated… facts on behind the lyrics for our song “Hard Times”.
the facts are: it’s all embarrassing & there was no “bright side”… hence the title, Hard Times.
thank you & goodnight.— hayley from Paramore (@yelyahwilliams) April 24, 2019
By comparison, “Behind the Lyrics” pulls in this sort of background information from Spotify’s partner, Genius — and Genius doesn’t always get things right. This, in fact, was the cause of a bit of an uproar recently, when Paramore singer Hayley Williams took to Twitter to yell at Spotify for running “outdated facts” on “Behind the Lyrics” — something she said her management team had tried to get changed for a year.
After her tweet went viral, Genius reached out to help. But following the incident, music fans pointed out other inaccuracies in “Behind the Lyrics,” including misstated facts on 21 Pilots’ song “Jumpsuit” and Travis Scott’s “Yosemite,” for example.

For Spotify, one possible solution to this problem could be to allow artists and their management teams to take control over what’s displayed as the song plays — while adopting the popular Stories format in the process. But at present, the Storyline feature is appearing on top of “Behind the Lyrics,” which is a bit odd and confusing.
We understand that Storyline is only a test for the time being on both iOS and Android, but not desktop. It’s available in the U.S. and in other markets, but Spotify isn’t commenting as to who may be seeing the test at this time or where.
If you are a part of the test group, you’ll see an indicator on the bottom of the screen that alerts you to the additional content. You can then swipe up anywhere on the screen that’s not a button in order to reveal the story and start tapping. The stories may contain lyrics, text or images.

For the time being, there’s no direct way for any artist or management team to contribute to Storyline. Those involved are working with Spotify directly. But it wouldn’t be unreasonable to think that the feature could be something that’s built into the Spotify Artist Dashboard in the future, if it proved to deliver the sort of positive engagement Spotify hopes to see.
The feature, if launched, would give Spotify its own sort of original content — an area that hadn’t fared so well in the past when Spotify was producing its own original videos, for example. And it would better cater to Spotify’s younger demographic who already understand and regularly use Stories in other social apps.
Android Police was first to spot the news (via Reddit), and found it was live on a handful of songs, including Jonas Brothers’ “Sucker” and several by Billie Eilish (“Bad Guy,” “Bury a Friend,” “When the Party’s Over,” “Wish You Were Gay”). We also understand it’s showing up on MAX’s “Love Me Less.” Plus, Reddit users claim to have seen on it 2 Chainz’ “Forgiven,” The Beaches’ “Snake Tongue,” and others.
Spotify confirmed in a brief statement to TechCrunch it’s testing Storyline.
“We are always testing new ways to create better experiences for more users,” a spokesperson said, when asked about the feature. The company didn’t offer any information about when it would roll out more broadly.
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Slack this morning disclosed estimated preliminary financial results for the first quarter of 2019 ahead of a direct listing planned for June 20.
Citing an addition of paid customers, the workplace messaging service posted revenues of about $134 million, up 66% from $81 million in the first quarter of 2018. Losses from operations increased from $26 million in Q1 2018 to roughly $39 million this year.
In addition to filing updated paperwork, the Slack executive team gathered on Monday to make a final pitch to potential shareholders, emphasizing its goal of replacing email within enterprises across the world.
“People deserve to do the best work of their lives,” Slack co-founder and chief executive officer Stewart Butterfield said in a video released alongside a live stream of its investor day event. “This desire of feeling aligned with your team, of removing confusion, of getting clarity; the desire for support in doing the best work of your life, that’s universal, that’s deeply human. It appeals to people with all kinds of roles, in all kinds of industries, at all scales of organization and all cultures.”
“We believe that whoever is able to unlock that potential for people … is going to be the most important software company in the world. We aim to be that company,” he added.”
Slack, valued at more than $7 billion with its last round of venture capital funding, plans to list on the NYSE under the ticker symbol “SK.”
The business filed to go public in April as other well-known tech companies were finalizing their initial public offerings. Following Uber’s disastrous IPO last week, public and private market investors alike will be keeping a close-eye on Slack’s stock market performance, which may determine Wall Street’s future appetite for Silicon Valley’s unicorns.
Though some of the recent tech IPOs performed famously, like Zoom, Uber and Lyft’s performance has served as a cautionary tale for going out in poor market conditions with lofty valuations. Uber began trading last week at below its IPO price of $45 and is today down significantly at just $36 per share. Lyft, for its part, is selling for $47.5 apiece today after pricing at $72 per share in March.
Slack isn’t losing billions per year like Uber, but it’s also not as close to profitability as expected. In the year ending January 31, 2019, Slack posted a net loss of $138.9 million and revenue of $400.6 million. That’s compared to a loss of $140.1 million on revenue of $220.5 million for the year ending January 31, 2018. In its S-1, the company attributed its losses to scaling the business and capitalizing on its market opportunity.
Workplace messaging startup Slack said Monday, February 4, 2019 it had filed a confidential registration for an initial public offering, becoming the latest of a group of richly valued tech enterprises to look to Wall Street. (Photo by Eric BARADAT / AFP) (Photo credit should read ERIC BARADAT/AFP/Getty Images)
Slack currently boasts more than 10 million daily active users across more than 600,000 organizations — 88,000 on the paid plan and 550,000 on the free plan.
Slack has been able to bypass the traditional roadshow process expected of an IPO-ready business, opting for a path to Wall Street popularized by Spotify in 2018. The company plans to complete in mid-June a direct listing, which allows companies to forgo issuing new shares and instead sell directly to the market existing shares held by insiders, employees and investors. The date, however, is subject to change.
Slack has previously raised a total of $1.2 billion in funding from investors, including Accel, Andreessen Horowitz, Social Capital, SoftBank, Google Ventures and Kleiner Perkins.
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Cloud kitchens are the big thing in food delivery, with ex-Uber CEO Travis Kalanick’s new business one contender in that space, with Asia, and particularly Southeast Asia, a major focus. Despite the newcomers, a more established startup from Singapore has raised a large bowl of cash to go after regional expansion.
Founded in 2014, Grain specializes in clean food while it takes a different approach to Kalanick’s CloudKitchens or food delivery services like Deliveroo, FoodPanda or GrabFood.
It adopted a cloud kitchen model — utilizing unwanted real estate as kitchens, with delivery services for output — but used it for its own operations. So while CloudKitchens and others rent their space to F&B companies as a cheaper way to make food for their on-demand delivery customers, Grain works with its own chefs, menu and delivery team. A so-called “full stack” model, if you can stand the cliched tech phrase.
Finally, Grain is also profitable. The new round has it shooting for growth — more on that below — but the startup was profitable last year, CEO and co-founder Yi Sung Yong told TechCrunch.
Now it is reaping the rewards of a model that keeps it in control of its product, unlike others that are complicated by a chain that includes the restaurant and a delivery person.
We previously wrote about Grain when it raised a $1.7 million Series A back in 2016, and today it announced a $10 million Series B, which is led by Thailand’s Singha Ventures, the VC arm of the beer brand. A bevy of other investors took part, including Genesis Alternative Ventures, Sass Corp, K2 Global — run by serial investor Ozi Amanat who has backed Impossible Foods, Spotify and Uber among others — FoodXervices and Majuven. Existing investors Openspace Ventures, Raging Bull — from Thai Express founder Ivan Lee — and Cento Ventures participated.
The round includes venture debt, as well as equity, and it is worth noting that the family office of the owners of The Coffee Bean & Tea Leaf — Sassoon Investment Corporation — was involved.
Grain covers individual food as well as buffets in Singapore
Three years is a long gap between the two deals — Openspace and Cento have even rebranded during the intervening period — and the ride has been an eventful one. During those years, Sung said the business had come close to running out of capital before it doubled down on the fundamentals before the precarious runway capital ran out.
In fact, he said, the company — which now has more than 100 staff — was fully prepared to self-sustain.
“We didn’t think of raising a Series B,” he explained in an interview. “Instead, we focused on the business and getting profitable… we thought that we can’t depend entirely on investors.”
And, ladies and gentleman, the irony of that is that VCs very much like a business that can self-sustain — it shows a model is proven — and investing in a startup that doesn’t need capital can be attractive.
Ultimately, though, profitability is seen as sexy today — particularly in the meal space, where countless U.S. startups have shuttered, including Munchery and Sprig — but the focus meant that Grain had to shelve its expansion plans. It then went through soul-searching times in 2017 when a spoilt curry saw 20 customers get food poisoning.
Sung declined to comment directly on that incident, but he said that company today has developed the “infrastructure” to scale its business across the board, and that very much includes quality control.
Grain co-founder and CEO Yi Sung Yong [Image via LinkedIn]
Grain currently delivers “thousands” of meals per day in Singapore, its sole market, with eight-figures in sales per year, he said. Last year, growth was 200 percent, Sung continued, and now is the time to look overseas. With Singha, the Grain CEO said the company has “everything we need to launch in Bangkok.”
Thailand — which Malaysia-based rival Dahamakan picked for its first expansion — is the only new launch on the table, but Sung said that could change.
“If things move faster, we’ll expand to more cities, maybe one per year,” he said. “But we need to get our brand, our food and our service right first.”
One part of that may be securing better deals for raw ingredients and food from suppliers. Grain is expanding its “hub” kitchens — outposts placed strategically around town to serve customers faster — and growing its fleet of trucks, which are retrofitted with warmers and chillers for deliveries to customers.
Grain’s journey is proof that startups in the region will go through trials and tribulations, but being able to bolt down the fundamentals and reduce burn rate is crucial in the event that things go awry. Just look to grocery startup Honestbee, also based in Singapore, for evidence of what happens when costs are allowed to pile up.
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Slack, the ubiquitous workplace messaging tool, will make its pitch to prospective shareholders on Monday at an invite-only event in New York City, the company confirmed in a blog post on Wednesday. Slack stock is expected to begin trading on the New York Stock Exchange as soon as next month.
Slack, which is pursuing a direct listing, will live stream Monday’s Investor Day on its website.
An alternative to an initial public offering, direct listings allow businesses to forgo issuing new shares and instead sell directly to the market existing shares held by insiders, employees and investors. Slack, like Spotify, has been able to bypass the traditional roadshow process expected of an IPO-ready business, as well as some of the exorbitant Wall Street fees.
Spotify, if you remember, similarly live streamed an event that is typically for investors eyes only. If Slack’s event is anything like the music streaming giant’s, Slack co-founder and chief executive officer Stewart Butterfield will speak to the company’s greater mission alongside several other executives.
Slack unveiled documents for a public listing two weeks ago. In its SEC filing, the company disclosed a net loss of $138.9 million and revenue of $400.6 million in the fiscal year ending January 31, 2019. That’s compared to a loss of $140.1 million on revenue of $220.5 million for the year before.
Additionally, the company said it reached 10 million daily active users earlier this year across more than 600,000 organizations.
Slack has previously raised a total of $1.2 billion in funding from investors, including Accel, Andreessen Horowitz, Social Capital, SoftBank, Google Ventures and Kleiner Perkins.
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Most of the strategy discussions and news coverage in the media and entertainment industry is concerned with the unfolding corporate mega-mergers and the political implications of social media platforms.
These are important conversations, but they’re largely a story of twentieth-century media (and broader society) finally responding to the dominance Web 2.0 companies have achieved.
To entrepreneurs and VCs, the more pressing focus is on what the next generation of companies to transform entertainment will look like. Like other sectors, the underlying force is advances in artificial intelligence and computing power.
In this context, that results in a merging of gaming and linear storytelling into new interactive media. To highlight the opportunities here, I asked nine top VCs to share where they are putting their money.
Here are the media investment theses of: Cyan Banister (Founders Fund), Alex Taussig (Lightspeed), Matt Hartman (betaworks), Stephanie Zhan (Sequoia), Jordan Fudge (Sinai), Christian Dorffer (Sweet Capital), Charles Hudson (Precursor), MG Siegler (GV), and Eric Hippeau (Lerer Hippeau).

“In 2018 I was obsessed with the idea of how you can bring AI and entertainment together. Having made early investments in Brud, A.I. Foundation, Artie and Fable, it became clear that the missing piece behind most AR experiences was a lack of memory.
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