Sleeper is looking to take on fantasy league apps from major players like ESPN and has amassed venture funding from Silicon Valley investors to take them down.

The Bay Area startup is aiming to treat a fantasy football league more like a social platform than a loose jumble of league mechanics, distinguishing itself as a simple and free, ad-free option.

Sleeper has done limited press as it has been ramping up its app over the past two seasons, but the team has been courting the interest of investors to scale the product, raising more than $7 million from VCs to date. The company closed a $5.3 million Series A late last year led by General Catalyst. In early 2017, the startup also closed a $2 million seed led by Birchmere Ventures with participation from Uber co-founder Garrett Camp’s startup studio, Expa.

There isn’t much in terms of monetization options at the moment. CEO Nan Wang tells TechCrunch that the focus right now is “amassing a large base of users and making it the stickiest and highest engagement product in the category.”

Wang says the app’s users spend 50 minutes per day on average during the season, numbers he calls “Instagram-like.” The main contributor to that number seems to be that chat is always a swipe away and that all of the actions that are happening during the season show up inside chats to encourage engagement.

This unifies the experience for users, many of whom have had to piecemeal their experience by using a WhatsApp or GroupMe group in addition to the other fantasy league apps that they’ve been using. Sleeper’s more differentiated UI seems to be largely popular among early vocal users as well as the up-to-the-minute notifications that deliver league updates.

Poaching users from other platforms is definitely a priority, but Wang says the team has really been looking at how to nab users who have stayed away from the convoluted confusion of fantasy leagues as well. Taking on the leading apps from ESPN, Yahoo and NFL can be daunting; another stress for the younger startup is just how tight the user acquisition window is, though things compound quickly if you can create one loyal user that brings their entire league to the platform.

“The user acquisition window for fantasy football leagues is strongest from the second week of August until the first week of September. Historically, we’ve seen that about 70% of users create their leagues in that three-week window,” Wang tells me.

The funding has been used to build out its team, which is still just 10 full-time employees, as well as expand their ambitions beyond fantasy football alone into other sports, including basketball and soccer.

Shout out to all the savvy enterprise software startuppers. Here’s a quick, two-part money-saving reminder. Part one: TC Sessions: Enterprise 2019 is right around the corner on September 5, and you have only two days left to buy an early-bird ticket and save yourself $100. Part two: for every Session ticket you buy, you get one free Expo-only pass to TechCrunch Disrupt SF 2019.

Save money and increase your ROI by completing one simple task: buy your early-bird ticket today.

About 1,000 members of enterprise software’s powerhouse community will join us for a full day dedicated to exploring the current and future state of enterprise software. It’s certainly tech’s 800-pound gorilla — a $500 billion industry. Some of the biggest names and brightest minds will be on hand to discuss critical issues all players face — from early-stage startups to multinational conglomerates.

The day’s agenda features panel discussions, main-stage talks, break-out sessions and speaker Q&As on hot topics including intelligent marketing automation, the cloud, data security, AI and quantum computing, just to name a few. You’ll hear from people like SAP CEO Bill McDermott; Aaron Levie, Box co-founder; Jim Clarke, director of Quantum Hardware at Intel and many, many more.

Customer experience is always a hot topic, so be sure to catch this main-stage panel discussion with Amit Ahuja (Adobe), Julie Larson-Green (Qualtrics) and Peter Reinhardt (Segment):

The Trials and Tribulations of Experience Management: As companies gather more data about their customers and employees, it should theoretically improve their experience, but myriad challenges face companies as they try to pull together information from a variety of vendors across disparate systems, both in the cloud and on prem. How do you pull together a coherent picture of your customers, while respecting their privacy and overcoming the technical challenges?

TC Sessions: Enterprise 2019 takes place in San Francisco on September 5. Take advantage of this two-part money-saving opportunity. Buy your early-bird ticket by August 16 at 11:59 p.m. (PT) to save $100. And score a free Expo-only pass to TechCrunch Disrupt SF 2019 for every ticket you buy. We can’t wait to see you in September!

Interested in sponsoring TC Sessions: Enterprise? Fill out this form and a member of our sales team will contact you.

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast, where we unpack the numbers behind the headlines.

Today is our promised Equity Shot (a short-form, single-topic episode) on the WeWork S-1. You can read Kate’s notes here, or Alex’s here as a place to start.

Given that we didn’t know when the WeWork S-1 filing was going to make itself known, we put together this episode from TechCrunch’s SF HQ, Alex’s home office and Kate inside a New York Blue Bottle Coffee. We were not about to let the locational issues stop us from having fun!

Where to begin! WeWork is growing like mad, but it’s hard to tell what its gross margins are. This makes its revenue quality hard to parse. (Alex tried to figure that out here, TechCrunch has even more good questions and notes here). What wasn’t hard to figure out was that WeWork — also known as The We Company — is tectonically unprofitable on operating and net bases. And that the company’s operations consume cash, while its investing activities torch the stuff.

WeWork’s eclectic chief executive officer and co-founder Adam Neumann will maintain a majority of voting rights. It’s not uncommon for founder-led companies to adopt this sort of voting structure, and, considering how central Neumann is to WeWork’s identity, we weren’t the least bit surprised by this.

The company’s IPO will make a lot of groups a lot of money. Mainly Benchmark, a respected venture capital fund, JP Morgan, and, of course, SoftBank, which has invested billions in WeWork and now owns more than 100 million shares.

And that’s all for now. Don’t miss our episode with Dan Primack that came out yesterday. A busy week, but a good one. Chat again soon!

In two years, Voyage has gone from a tiny self-driving car upstart spun out of Udacity to a company able to operate on 200 miles of roads in retirement communities.

Now, Voyage is on the verge of introducing a new vehicle that is critical to its mission of launching a truly driverless ride-hailing service. (Human safety drivers not included.)

This internal milestone, which Voyage CEO Oliver Cameron hinted at in a recent Medium post, went largely unnoticed. Voyage, after all, is just a 55-person speck of a startup in an industry, where the leading companies have amassed hundreds of engineers backed by war chests of $1 billion or more. Voyage has raised just $23.6 million from investors that include Khosla Ventures, CRV, Initialized Capital and the venture arm of Jaguar Land Rover.

Still, the die has yet to be cast in this burgeoning industry of autonomous vehicle technology. These are the middle-school years for autonomous vehicles — a time when size can be misinterpreted for maturity and change occurs in unpredictable bursts.

The upshot? It’s still unclear which companies will solve the technical and business puzzles of autonomous vehicles. There will be companies that successfully launch robotaxis and still fail to turn their service into a profitable commercial enterprise. And there will be operationally savvy companies that fail to develop and validate the technology to a point where human drivers can be removed.

Voyage wants to unlock both.

Crowded field

What happens when two former spies meet the startup world? We’re about to find out.

We’re pleased to announce former National Security Agency director Adm. Mike Rogers will be at Disrupt SF on October 2-4. The former U.S. intelligence head oversaw the shadowy agency during one of its most tumultuous times in its history in the aftermath of the massive leak of classified documents by whistleblower Edward Snowden. He also oversaw the Pentagon’s cyberwar-fighting division, U.S. Cyber Command, amid Russian interference during the 2016 presidential election.

Since leaving the world of intelligence, Rogers became a senior advisor at Team8, a leading cybersecurity think tank and company creation platform, which helps to build cybersecurity companies from the ground up.

We’re also thrilled to announce Team8 founder Nadav Zafrir will join Rogers onstage at Disrupt, where both will discuss what they can bring to the world of security startups from their extensive intelligence and cybersecurity backgrounds.

Zafrir served as the commander of the elite technology and intelligence division Unit 8200, Israel’s equivalent of the NSA. Since leaving the unit, Zafrir founded Team8 to help cybersecurity companies go from idea to execution.

Team8 recently opened a New York headquarters, with Rogers serving as a key part of the U.S. expansion. To date, the think tank has enlisted several major investors, including Microsoft, Walmart and SoftBank.

Rogers and Zafrir will discuss what they learned from their time working in the intelligence space and what they bring to the startup world, and they’ll look ahead at the cybersecurity landscape and discuss what comes next.

Disrupt SF runs October 2 – October 4 at the Moscone Center in San Francisco. Tickets are available here!

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Sramana Mitra: To be perfectly honest with you, I flatly turn down all of these requests. Corbett Drummey: One of the cool things about Popular Pays is that although a brand can use our search tool...

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Skip is beginning to test the first electric scooter that the startup built entirely in-house. They’re not quite ready for prime time, but Skip expects to deploy them in San Francisco this October.

That’s notably when San Francisco plans to allow service providers to deploy electric scooters as part of the city’s first permanent permitting program. Skip’s current permit expires on October 14, but the company plans to reapply for a permit, Skip CEO Sanjay Dastoor told TechCrunch.

For riders, they will likely notice the sheer difference in the size of this scooter compared to Skip’s previous models. Skip’s S3 is much larger than the company’s previous models in order to help riders feel more stable and secure on the scooter. The S3 also ditches the regenerative brake for a traditional hand brake and rear foot brake.

This comes shortly after Skip announced it would bring back its scooters to Washington, D.C. following some battery-related issues that led to fires.

The scooter fire in D.C. was caused by a damaged battery, though, it’s not clear if it was intentional or accidental. With this new scooter model, the battery was custom built for the shared electric scooter service use case and is also completely enclosed, which should help prevent it from getting damaged, Dastoor said.

This swappable battery should also help with unit economics, given that it won’t need to be replaced as often. The battery pack, Dastoor said, can last for about 20 rides, with a range of 35 miles per charge. The custom battery also features diagnostic capabilities that can detect if it’s wet. Though, the battery is designed to be able to survive submerged in 1 meter of water for up to 30 minutes.

“What we’re looking at now is how do we actually do the swap,” Dastoor said. “We’re changing the model from taking vehicles off of the road to swapping out the batteries.”

Dastoor said he currently envisions a warehouse with a bunch of electric vehicles lined up charging the batteries. Given that the current model relies on independent contractors to take vehicles home to charge them, you could imagine a world in which the independent contractors instead are responsible for picking up fresh batteries at the warehouse and then swapping them out with the depleted ones.

Previous models of Skip’s scooters had swappable batteries and even cameras, but the cameras didn’t make it into the new version.

“We are testing a variety of sensor systems to solve some of our key priorities, like parking compliance, rider safety and etiquette, and reliable location tracking,” Dastoor said in a follow-up email.

And thanks to the modular design of the scooter, Skip can easily add and remove elements, such as cameras, locks and even regenerative braking.

No startup is as polarizing as WeWork, and for good reason. The company, whose relentless growth has seen it open 528 locations across 111 cities in just about nine years, has never been entirely forthcoming on exactly how the unit economics add up at its locations. And so we have had a beautiful Rorschach test for the financial class these past few years regarding the company: it’s either the greatest financial return of all time or a Ponzi scheme (and absolutely nothing  in between dammit).

That ambiguity is supposed to change with the company’s S-1, where it is required by law to show a reasonably comprehensive set of numbers to investors in order to go public. Unfortunately, despite all the verbiage (“Our mission is to elevate the world’s consciousness.”) and data, we still don’t know the health of the core of the company’s business model or fully understand the risks it is undertaking. 

Here are three questions that remain unanswered so far by the company’s filing.

No cohort data on contribution margin

As I pointed out a couple of months ago, the ability for investors to understand the true unit economics of WeWork’s business is critical for cutting through the debate over its financial future.

It’s not as though WeWork hasn’t tried to give us some insight in its S-1. One of WeWork’s core operating metrics is “contribution margin including non-cash GAAP straight-line lease cost” (or what I will abbreviate just this one time as CMINCGAAAPSLLC). Through this metric, the company offers us a single number into the health of its business — essentially a way for investors to understand the performance of the company’s mature office locations.

Obviously, not everyone owns a boat, and boat ownership is far more unique than car ownership — which makes it maybe an ideal category for peer-to-peer marketplace rentals. P2P boat rental startup Boatsetter recognized this opportunity, and is now announcing a $10 million Series A “extension” funding round to help it grow its business, with investment led by WestCap Group and Valor Equity.

Boatsetter counts itself the top peer-to-peer boat rental marketplace in the U.S., and offers insurance to boat renters, owners and captains alike through a just-announced strategic partnership with Geico. The Miami-based startup estimates the size of the peer-to-peer boat rental market at as much as $50 billion annually, and plans to use its investment to expand its offering, both from a product perspective and expanding its presence in key markets globally.

To date, Boatsetter has raised $31 million, including earlier portions of this Series A raised over the past two years. The company focuses on rentals for anywhere from two to more than a dozen passengers, and a range of boat options that can also include qualified captains for larger vessels. It’s a bit like an Airbnb crossed with an Uber, and there are rentals available in vacation hotspots around the world. As part of this new funding, Boatsetter is also adding a new board member — Laurence Tosi, the former CFO of Blackstone and Airbnb, who is also a founder and partner at new investor WestCap.

The funding will help the startup invest in bringing in new talent focused on design, engineering and brand building, in addition to product work and market expansion.

Enterprise carpooling startup Scoop just closed a $60 million round led by Activate Capital, with participation from Goldman Sachs, NGP Capital, Total Group, BNP Capital and others to fuel its expansion and growth. This round brings Scoop’s total funding to $106 million.

Scoop, which launched back in 2015, is a corporate carpooling service that works with the likes of LinkedIn, Workday, T-Mobile and more than 50 other companies to help their employees get to and from work.

With Scoop, trips are pre-scheduled, so you can select from one or more times you’d be willing to leave in the morning and afternoon, and have up until 9pm the night before for morning trips and 3:30pm the day of for afternoon trips to schedule your ride. After the deadline, Scoop’s algorithms work to automatically create the most efficient carpools based on routes, detours, company preference, favorites and more.

Currently, Scoop operates in more than 2,000 cities across six major metro areas, including the San Francisco Bay Area, Seattle, Portland, Reno and Los Angeles. To date, Scoop has facilitated 7 million carpool trips.

Scoop is not the only, nor the first, company to do carpooling. Lyft, for example, began as a carpooling service called Zimride, which is now owned by Enterprise. There’s also Carma, which partners with federal and state transportation agencies.

Late last year, Scoop partnered with Lyft to supplement its offerings to its customers. That partnership has continued into the present day.

“By partnering together, Scoop and Lyft are ensuring that commuters not only gain a stronger sense of community by carpooling to work with co-workers and neighbors, but that they also feel supported in the event of last-second schedule changes and know they have guaranteed transportation home,” Scoop co-founder and CEO Rob Sadow said in a statement to TechCrunch. “With this program, carpoolers are able to request a Lyft or view public transit options through the Scoop app.”

According to a recent report, the global security and vulnerability market is estimated to grow 10% through the year 2023. Earlier this month, Rapid7 (Nasdaq: RPD), a leading player in the industry,...

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Just a couple of months after disclosing a $15 million round of funding, vCita, the business management SaaS for SMEs, has made an acquisition: It’s acquiring WiseStamp, a veteran of the Israeli startup scene that launched its email marketing tool a decade ago.

Unsurprisingly, terms of the deal remain undisclosed. However, I understand that vCita has acquired WiseStamp as a company, including all assets, employees, customer base, technology and other IP. In addition, WiseStamp’s two remaining founders will join vCita along with the rest of the 20-person team.

WiseStamp hadn’t taken much capital in its relatively long history, having raised around $400,000 from angel investors.

Founded in 2009 by Orly Izhaki, Tom Piamenta, Tzvika Avnery and Sasha Gimelshtein, WiseStamp offers a email signature solution for self-employed professionals. The company claims over 50,000 paying customers, who it says use the platform to increase social media engagement, expand business reach, and generate more sales.

Meanwhile, the much younger vCita says it has more than 100,000 paying users worldwide who use its SaaS to manage their schedule, track invoices, collect payments and organize client data via the vCita app.

“We’re thrilled to have WiseStamp join our team. Both companies share the same vision: Empowering small business owners to deliver their services at a level comparable to that of a large company, at a fraction of the cost,” says says vCita co-founder and CEO Itzik Levy in a statement.

Adds Orly Izhaki, WiseStamp’s CEO and co-founder: “Over the years, WiseStamp created advanced solutions that enable hundreds of thousands of small enterprises to grow their business online. We are excited about the merger, which will establish us as one of the most dominant players in the SMB market.”