BigBrain aims to bring live mobile trivia back to glory

If you ask Nik Bonaddio why he wanted to build a new mobile trivia app, his answer is simple.

“In my life, I’ve got very few true passions: I love trivia and I love sports,” Bonaddio told me. “I’ve already started a sports company, so I’ve got to start a trivia company.”

He isn’t kidding about either part of the equation. Bonaddio actually won $100,000 on “Who Wants To Be A Millionaire?”, which he used to start the sports analytics company numberFire (acquired by FanDuel in 2014).

And today, after a period of beta testing, Bonaddio is launching BigBrain. He’s also announcing that the startup has raised $4.5 million in seed funding from FirstRound Capital, Box Group, Ludlow Ventures, Golden Ventures and others.

Of course, you can’t mention mobile trivia without thinking of HQ Trivia, the trivia app that shut down last year after some high-profile drama and a spectacular final episode.

BigBrain

Image Credits: BigBrain

But Bonaddio said BigBrain is approaching things differently than HQ in a few key ways. For starters, although there will be a handful of free games, the majority will require users to pay to enter, with the cash rewards coming from the entry fees. (From a legal perspective, Bonaddio said this is distinct from gambling because trivia is recognized as a game of skill.)

“The free-to-play model doesn’t really work for trivia,” he argued.

In addition, there will be no live video with a live host — Bonaddio said this would “very, very difficult from a technical perspective and very cost ineffective.” Instead, he claimed the company has found a middle ground: “We have photos, we have different interactive elements, it’s not just a straight multiple choice quiz. We do try to keep it interactive.”

Plus, the simpler production means that where HQ was only hosting two quizzes a day, BigBrain will be hosting 20, with quizzes every 15 minutes at peak times.

Topics will range from old school hip hop to college football to ’90s movies, and Bonaddio said different quizzes will have different prize structures — some might be winner take all, while others might award prizes to the top 50% of participants. The average quiz will cost $2 to $3 to enter, but prices will range from free to “$20 or even $50.”

What kind of quiz might cost that much money to enter? As an example, Bonaddio said that in a survey of potential users, he found, “There are no casual ‘Rick and Morty’ fans … They’re almost completely price sensitive, and since they’ve seen every episode, they can’t fathom a world where someone knows more about ‘Rick and Morty’ than they do.”

Daily Crunch: Europe charges Apple with antitrust breach

Apple faces an antitrust complaint in Europe, TikTok has a new CEO and YouTube TV disappears from Roku. This is your Daily Crunch for April 30, 2021.

Also, this is my last day at TechCrunch, and therefore my last day writing The Daily Crunch. It’s been a blast rounding up the news for all of you, and thank you to everyone who took the time to tell me they enjoyed the newsletter.

On Monday, TechCrunch will be debuting a more collaborative approach to The Daily Crunch — stay tuned!

The big story: Europe charges Apple with antitrust breach

The European Commission has filed preliminary charges against Apple, focusing on complaints by Spotify that Apple’s App Store policies — particularly its requirements around in-app purchase — are anti-competitive.

“The Commission takes issue with the mandatory use of Apple’s own in-app purchase mechanism imposed on music streaming app developers to distribute their apps via Apple’s App Store,” it wrote. “The Commission is also concerned that Apple applies certain restrictions on app developers preventing them from informing iPhone and iPad users of alternative, cheaper purchasing possibilities.”

Apple has 12 weeks to respond to the charges.

The tech giants

ByteDance CFO assumes role as new TikTok CEO — Eight months after former TikTok CEO Kevin Mayer quit in the midst of a full-court press from the Trump administration, TikTok finally has a new permanent leader.

Roku removes YouTube TV from its channel store following failed negotiations — Earlier this week, Roku warned customers that the YouTube TV app may be removed from its streaming media players and TVs, and it alleged that Google was leveraging its monopoly power during contract negotiations to ask for unfair terms.

Computer vision inches toward ‘common sense’ with Facebook’s latest research — One development Facebook has pursued in particular is what’s called “semi-supervised learning.”

Startups, funding and venture capital

Developer-focused video platform Mux achieves unicorn status with $105M funding — “I think video’s eating software, the same way software was eating the world 10 years ago.”

As concerns rise over forest carbon offsets, Pachama’s verified offset marketplace gets $15M — The startup is building a marketplace for forest carbon credits that it says is more transparent and verifiable thanks to its use of satellite imagery and machine learning technologies.

Heirlume raises $1.38M to remove the barriers of trademark registration for small businesses — Heirlume’s machine-powered trademark registration platform turns the process into a self-serve affair that won’t break the budget.

Advice and analysis from Extra Crunch

Optimism reigns at consumer trading services as fintech VC spikes and Robinhood IPO looms — But services that help consumers trade might need to retool their models over time to ensure long-term income.

Amid the IPO gold rush, how should we value fintech startups? — If there has ever been a golden age for fintech, it surely must be now.

The health data transparency movement is birthing a new generation of startups — Twin struggles seem to be taking place: a push for more transparency on provider and payer data, and another for strict privacy protection for personal patient data.

(Extra Crunch is our membership program, which helps founders and startup teams get ahead. You can sign up here.)

Everything else

Cloud infrastructure market keeps rolling in Q1 with almost $40B in revenue — That’s up $2 billion from last quarter and up 37% over the same period last year.

The second shot is kicking in — A new episode of the Webby-nominated Equity podcast.

Pitch your startup to seasoned tech leaders, and a live audience, on Extra Crunch Live — We’re bringing the pitch-off format to Extra Crunch Live.

The Daily Crunch is TechCrunch’s roundup of our biggest and most important stories. If you’d like to get this delivered to your inbox every day at around 3pm Pacific, you can subscribe here.

Roc Nation’s VC Neil Sirni lays out his investment strategy

Jay-Z’s Roc Nation announced in 2017 that it was forming a venture investment arm called Arrive. And the firm has been busy since then — co-founder and President Neil Sirni said Arrive has made 29 investments thus far.

At the same time, Sirni hasn’t really said much about those investments publicly, or about the broader strategy. So he reached out to me a few months ago, suggesting that he was ready to provide more details about Arrive.

“We’re now three years, 29 investments in and expanding – so it felt like the right time to start opening up a bit,” he said.

Over the course of a few back-and-forth emails, we discussed how Arrive fits into the larger aims of Roc Nation, how Sirni (a former Goldman Sachs executive) makes investment decisions and where he’s focusing next. (Spoiler: Southeast Asia is a big part of that answer.)

He was also eager to provide testimonials from Arrive’s portfolio companies — for example, Outlier.org founder Aaron Rasmussen said that “when Arrive commits to your mission, they commit,” while Helm co-founder and CEO Giri Sreenivas said that the firm “brings something that I don’t see in traditional institutional investors – legitimate operational expertise around brand and marketing.”

You can read our email Q&A, lightly edited for length and style, below.

What is Arrive and how does it fit into the larger Roc Nation umbrella?

Arrive is Roc Nation’s venture platform. Roc Nation is a full-service music and sports management, music publishing and entertainment company founded by Jay-Z. Roc Nation and its affiliated companies have built a diversified business that employs several hundred people. These businesses include artist and athlete representation, a portfolio of spirit brands, an apparel line, a philanthropy division that manages four charitable organizations, a content streaming service, a digital team that oversees social media accounts with over 1.4 billion followers, a sales and marketing division that works on countless partnerships with Fortune 500 companies, communications, video production and live event production, among others.

The Roc Nation infrastructure can add value to many different types of businesses across various stages, which is why we created Arrive. For consumer-facing businesses, Arrive leverages the Roc Nation infrastructure to help companies with branding, creative, marketing, communications, and other services. For enterprise, we use our broad network of B2B relationships to help with business development.

Being a strategic venture investor on the cap table of a portfolio company is not only about the investment but also how much human capital a fund can deploy to drive long-term, real and unique value for entrepreneurs and their businesses. So, we’re leveraging the broader Roc Nation platform to help portfolio companies and, in turn, receiving access to great entrepreneurs.

What kinds of investments do you normally make — types of companies, size of investment, etc?

We’re relatively sector and stage agnostic. We have dedicated capital in an early-stage fund that tends to focus on Series A to Series C, but we’ve also started to SPV growth and pre-IPO investments as we lay the foundation for a dedicated growth vehicle later this year.

How do you make investment decisions? Is Jay-Z involved in the process?

We gravitate toward companies that we can provide meaningful assistance to but that are outside of Roc Nation’s core industries of music and traditional sports. Thanks to our platform, that is an extremely broad opportunity set. To date, we’ve made 29 investments under the Arrive umbrella in everything from fintech, insurtech, edtech, health & wellness, social, and gaming. Geographically, we’re investing roughly 80% in North America, primarily the US, and 20% across Southeast Asia, namely, Singapore, Indonesia, and Vietnam. As a strategic investor, we never lead deals and always co-invest.

Our long-term focus is on driving real and unique value for our portfolio companies. If we remain hyper-focused on this mission, we believe we have the opportunity to build an enduring brand as a top tier strategic investor.

Jay-Z approves every Arrive opportunity; he, Juan Perez, and Desiree Perez are overwhelmingly supportive of Arrive and what we’re collectively trying to accomplish.

TechCrunch: What’s your biggest success story so far?

Neil Sirni: I’m very proud of being co-founder of Arrive and what it took to get here. In the grand scheme of things, we’re just getting started, but I’ve been an entrepreneur — after leaving a large public company — for over 10 years now. It’s been a roller coaster with many sacrifices, but I can understand and relate to our founders and their journey which makes this experience even more rewarding. The founders of Roc Nation have built their businesses brick by brick as well, so the entire organization is united by this entrepreneurial mindset. I still consider myself a founder and operator first, whose business happens to be making investments.

NEW YORK, NY – OCTOBER 20: Jay Z performs during Tidal X: 1020 at Barclays Center on October 20, 2015 in the Brooklyn borough of New York City. (Photo by Taylor Hill/FilmMagic)

Given that Arrive has been around for a few years, what made you feel like this is the time to start talking more openly about the fund?

When Arrive launched a few years ago, I hated the idea of talking about what we’re going to do. Instead, we wanted to quietly actually go do it; learn, improve, build and, in the process, demonstrate that we’re not, and never will be, tourists in the venture ecosystem. We’re now three years, 29 investments in and expanding – so it felt like the right time to start opening up a bit.

What’s an example of an investment where working with Arrive/Roc Nation led to gains beyond the financial investment?

Arrive functions like many other investors in that we spend time understanding a company’s vision and then try to provide them meaningful levers to pull to help drive their success. Our toolkit is unique thanks to the Roc Nation platform and network. We’ve found that both our portfolio companies and their other investors, typically traditional venture funds, find those levers complementary and additive to the cap table.

Arrive typically works with portfolio companies across three main areas. The first is creative and brand marketing.  The second is business development and partnerships. The third is communications.

Communications efforts are generally focused on driving short-term or immediate awareness. Many of our portfolio companies receive broader press coverage when we invest in them. That initial attention typically dies down within a week or two although those news stories remain as searchable assets that the company might not otherwise have. While this can be of some value, especially for consumer businesses, we believe it’s at the bottom of the list compared to the long-term benefits that can be derived from Roc Nation’s underlying infrastructure in brand marketing and business development.

In terms of creative and brand marketing, we’ve likely saved our earlier stage portfolio, in aggregate, over a million dollars by providing brand and agency work at no cost.  Examples of this include campaign ideation, graphic design, video production, hosting live events, and product integrations, among other activities.

For business development and partnerships support, we have leveraged our network to help portfolio companies launch their own internal philanthropic platforms, leveraged our B2B relationships to introduce new partners and customers, brought in other strategic investors in a targeted way, helped companies navigate endorsement deals, and recruited non-technical executive talent to join their companies.

We don’t pretend to be a magic bullet, no investor can be, but we’re focused on continuously improving and building on the services that we provide to our portfolio companies. The founder journey is never a straight line and we pride ourselves on being willing to do whatever we can on their behalf. Stephen Francis, SVP at Arrive, and I are accessible to our portfolio companies any day and time.

Do you see these investments as primarily strategic for Roc Nation, or are you focused on financial returns?

‘Strategic’ investor, in the context of Arrive, refers to the strategic value that we bring to the cap table of a portfolio company.  We leverage that strategic value to get into deals and form relationships with entrepreneurs in whom we have high conviction.  Our ultimate goal is financial return and Arrive’s investments are not meant to be strategic in nature for Roc Nation as an operating company. Instead, an investment from Arrive is meant to be strategic for the portfolio company.

You said you’re stage agnostic with capital devoted to different stages. Can you say anything more what the breakdown is in terms of early stage vs. later growth deals, and how that might change with the new growth fund?

Of our 29 investments, I would classify 25 as early stage and 4 as growth.  In regards to percentage of capital, the 4 growth investments account for a little over 35% of total capital deployed. When we do have a dedicated growth fund, I expect the volume of growth investments to pick up to roughly 3 – 6 per year.

 What are your priorities for 2021?

At a high level our priorities are to build out a larger team to ensure that we’re staying very engaged with the portfolio as we scale and to continue being aggressive in deploying more capital to back great companies.

On a more granular level I’m looking forward to physically getting back to Southeast Asia, namely Singapore, Indonesia and Vietnam, on a regular basis. We’re really bullish on the region and believe it’s only a matter of time before more venture funds deploy significant capital there. We started to invest a lot of time there in 2019 as part of our plan to deploy roughly 30% of our early-stage fund in the region. That expansion has been hindered by COVID-19. However, I’ll make quarterly trips once travel normalizes. There is nothing like in-person interaction to build relationships and trust, especially internationally.

Daily Crunch: Biden’s labor secretary says gig workers should be reclassified

The Biden administration hints at gig economy changes, Blue Origin will be taking passengers and we interview Jim Belushi about weed. This is your Daily Crunch for April 29, 2021.

The big story: Biden’s labor secretary says gig workers should be reclassified

The Biden administration’s labor secretary Marty Walsh recently said in an interview with Reuters that he’s “looking at” the gig economy.

“In a lot of cases gig workers should be classified as employees,” Walsh said. “In some cases they are treated respectfully and in some cases they are not and I think it has to be consistent across the board.”

For now, this is just talk, but it suggests that new regulations and gig work reclassification could be a priority for the new administration.

The tech giants

Google Pay update adds grocery offers, transit expansions and spending insights — Through partnerships with Safeway and Target, Google Pay users will now be able to browse their store’s weekly circulars showcasing the latest deals.

Zynga and Rollic acquire the hyper-casual game studio behind High Heels — The company said High Heels (or, if you insist, High Heels!) has been downloaded more than 60 million times since it launched in January.

IBM is acquiring cloud app and network management firm Turbonomic for up to $2B — Turbonomic provides tools to manage application performance, along with Kubernetes and network performance.

Startups, funding and venture capital

Blue Origin will start selling tickets for New Shepard space tourism flights on May 5 — The “when and how much” are the two burning questions that remain around the Jeff Bezos-backed space company’s first commercial passenger flights.

TravelPerk raises $160M in equity and debt after a year of derailed business trips — TravelPerk lets users compare, book and invoice trains, cars, flights, hotels and apartments from a range of providers.

MoviePass co-founder’s PreShow Interactive raises $3M to expand into gaming — The startup will give PC and console gamers a new way to earn in-game currency in exchange for watching ads.

Advice and analysis from Extra Crunch

Healthcare is the next wave of data liberation — David Jegen and Carl Byers of F-Prime Capital argue that the winners of the healthcare data transformation will look different than they did with financial data.

Fintech startups set VC records as the 2021 fundraising market continues to impress — New data indicate Q1 2021 was the biggest fintech VC quarter ever.

How to fundraise over Zoom more effectively — A year ago, many of us probably thought that virtual fundraising would be impossible.

(Extra Crunch is our membership program, which helps founders and startup teams get ahead. You can sign up here.)

Everything else

Jim Belushi is chasing the magic in cannabis — We interviewed Belushi about his new greenhouses, supplied in part by GrowGeneration.

U.S. video game spending increased 30% in Q1 — Content was up 25% for the quarter, accessories jumped 42% and hardware went up 82%, according to NPD.

Sequoia’s Shaun Maguire and Vise’s Samir Vasavada will talk success in fintech on Extra Crunch Live — Join us on May 19 to discuss what brought the pair together, key tips for fundraising and how to be successful in the fintech space.

The Daily Crunch is TechCrunch’s roundup of our biggest and most important stories. If you’d like to get this delivered to your inbox every day at around 3pm Pacific, you can subscribe here.

Digital comics startup Madefire is shutting down

R.I.P. Madefire, a startup that recruited high-profile artists to reinvent comics for new formats and platforms.

An announcement on the Madefire website states the company entered into “an assignment of benefit for creditors” (explained as “a state-level insolvency proceeding similar to bankruptcy”) earlier this month, which was then reported this morning in The Beat. As a result, no new books will be published, users will not be able to purchase any additional books and they’re also encouraged to download all their purchased content before the end of the month.

This news affects other apps built with Madefire’s technology. The Archie comics app has shut down as well, with the publisher writing, “We realize this comes as a surprise and we are making every effort to do right by our loyal customer base,” specifically by offering readers a free one-month subscription to Comixology Unlimited. (Amazon acquired digital comics platform Comixology in 2014, launching an Unlimited subscription service two years later.)

Madefire first launched in 2012, back when publishers were experimenting with formats like motion comics. The company described its titles as “motion books,” combining the animation and effects of motion comics with a more traditional reading experience.

“Motion comics are a passive experience, a watching experience that is tantamount to bad animation – it’s like watching a movie,” co-founder and CEO Ben Wolstenholme said at the time. “Motion Books is a reading experience, actively controlled by the reader – it’s like reading a book. Our goal is to be the best reading experience developed for the iPad.”

Perhaps the most impressive thing about the company was the artists it had enlisted before launch, including Dave Gibbons and Bill Sienkiewicz.

More recently, Madefire announced partnerships with other tech platforms, including Snapchat and troubled augmented reality company Magic Leap.

According to Crunchbase, Madefire had raised $16.4 million in funding from investors including True Ventures, Plus Capital, Kevin Spacey (yes, that Kevin Spacey) and Drake, but The Beat reports that the total was “even more than that.”

Zynga and Rollic acquire the hyper-casual game studio behind High Heels

Last year, Zynga bought hyper-casual game maker Rollic. Today, Rollic is a Zynga subsidiary, and it’s announcing the acquisition of another game studio called Uncosoft.

Like Rollic, Uncosoft develops hyper-casual games and is based in Turkey (Istanbul in Rollic’s case, Izmir in Uncosoft’s). In fact, Rollic has already published a couple of Uncosoft games, most notably High Heels, in which the player navigates an obstacle course in increasingly ridiculous high heels — the company said High Heels (or, if you insist, High Heels!) has been downloaded more than 60 million times since it launched in January, and it’s even been praised for bringing “queer joy to the top of the App Store charts.”

Rollic co-founder and CEO Burak Vardal told me that when you’re in the hyper-casual gaming business, you’re “always looking for product-oriented teams.” And it sounds like Vardal is impressed by what he’s seen of the Uncosoft team, making him confident that it can successfully build “new titles like High Heels.”

“Producing a game together as development studio and publisher, you already start working like a merged company,” he said. “You argue about game design all day, you share strategies […] and you — not on purpose — start learning about how that company operates, how are the founders, how is the art team.”

Meanwhile, Uncosoft CEO Edip Enes Çakır said in a statement that there has been “unprecedented harmony” between the two teams as they’ve worked together in recent years, and that “our culture and vision of making global games will be augmented with the expertise of Rollic and Zynga.”

Rollic was actually Zynga’s fourth acquisition in Istanbul, so it’s clear that the city and country are becoming a bit of a hub. Vardal said Rollic does have partners outside of Turkey, but he suggested that the country has been particularly successful with hyper-casual games because of its huge student population.

Verdal also suggested that High Heels points to a path that other hyper-casual games might follow to success: namely, TikTok.

“The animations of the game and the character mechanic are what we call TikTok-able,” he said. “It had a huge impact in Gen Z and huge organic reach in TikTok […] The new generation wants content that feeds that ecosystem.”

The financial terms of the acquisition were not disclosed.

Daily Crunch: Uber adds vaccine booking

Uber unveils half a dozen new features, Samsung announces a new flagship laptop and Zomato files to go public. This is your Daily Crunch for April 28, 2021.

The big story: Uber adds vaccine booking

Uber announced a half dozen new features today, including the ability to make a vaccine appointment at Walgreens and then reserve a ride to get there.

Other additions include a valet service to drop off rental cars, reserved rides at airports and the ability to pick up food during a ride. In an interview, CPO Sundeep Jain suggested that these features are part of the company’s key focus for the past year, namely “helping users ‘go’ and helping users ‘get.’”

The tech giants

Here’s Samsung’s new flagship laptop series, the Galaxy Book Pro — These Windows machines continue the company’s push to blur some of the productivity lines between its Galaxy PC and mobile offerings.

Facebook hides posts calling for PM Modi’s resignation in India — Facebook temporarily hid all posts with the hashtag “ResignModi” in India, although a spokesperson said those posts have now been restored.

Netflix launches its shuffle feature, now called ‘Play Something,’ to users worldwide — This should make it easier to find something to watch when you can’t make a decision on your own.

Startups, funding and venture capital

Alchemy raises $80M at a $505M valuation to be the ‘AWS for blockchain’ — The company describes itself as the backend technology behind the blockchain industry.

MessageBird acquires SparkPost for $600M using $800M Series C extension — The acquisition enables MessageBird to get a stronger foothold in the U.S. market.

Splitwise raises $20M Series A to help everyone in the world divvy expenses — Splitwise aims to reduce the stress and awkwardness that money puts on relationships of all sorts.

Advice and analysis from Extra Crunch

Zomato juice: Indian unicorn’s proposed IPO could drive regional startup liquidity — Zomato’s debut could lead to a liquidity rush in India.

Dear Sophie: What’s the latest on DACA? — The latest edition of “Dear Sophie,” the advice column that answers immigration-related questions about working at technology companies.

Fund managers can leverage ESG-related data to generate insights — Apex Group’s Georges Archibald argues that environmental, social and governance insights can yield treasure in the form of alternative data.

(Extra Crunch is our membership program, which helps founders and startup teams get ahead. You can sign up here.)

Everything else

CES will return to Las Vegas in 2022 — Per a press release, roughly 1,000 companies have committed to returning.

India’s entrepreneurs and investors are mobilizing to help the nation fight COVID-19, and you can too — For a week straight, India has reported more than 300,000 daily new infections, about half of all the cases across the globe.

Porsche makes its case for an all-electric Taycan wagon — The Porsche Taycan 4 Cross Turismo offers a blend of practicality with a whole lot of power and speed for under $100,000.

The Daily Crunch is TechCrunch’s roundup of our biggest and most important stories. If you’d like to get this delivered to your inbox every day at around 3pm Pacific, you can subscribe here.

Daily Crunch: Spotify adds support for paid podcasts

Spotify launches paid podcast support, Amazon announces new tablets and we unveil the agenda for TC Sessions: Mobility. This is your Daily Crunch for April 27, 2021.

The big story: Spotify adds support for paid podcasts

As first announced in February, Spotify is now allowing podcasters to offer subscriber-only content, published through its Anchor podcasting software. Creators choose from three subscription tiers — $2.99, $4.99 or $7.99 per month.

This comes one week after Apple announced support for paid podcast subscriptions. But where Apple said it would take 30% of first-year subscriptions and 15% after that, Spotify says it will pass 100% of revenue on to podcasters for the first two years, only charging a 5% fee starting in 2023.

The tech giants

Amazon announces new Fire tablets and kids editions — The Fire HD 10 is thinner and lighter than its predecessor, with pricing starting at $150.

Tesla wants to make every home a distributed power plant — CEO Elon Musk said he wants to turn every home into a distributed power plant that would generate, store and even deliver energy back into the electricity grid, all using the company’s products.

Red Hat CEO looks to maintain double-digit growth in second year at helm — Red Hat CEO Paul Cormier runs the centerpiece of IBM’s transformation hopes.

Startups, funding and venture capital

Kids-focused fintech Greenlight raises $260M in a16z-led Series D, nearly doubles valuation to $2.3B — Since it launched its debit cards for kids in 2017, the company has set up accounts for more than 3 million parents and children.

Kry closes $312M Series D after use of its telehealth tools grows 100% yoy — During the pandemic, Kry quickly stepped in to offer a free service for doctors to conduct web-based consultations.

Banana Capital’s debut fund is for internet-first founders — You might know him for his viral tweets, but Turner Novak wasn’t always a master meme-maker.

Advice and analysis from Extra Crunch

Internal rates of return in emerging US tech hubs are starting to overtake Silicon Valley — AngelList analyzed IRR for almost 2,500 deals dating back to 2013.

Fifth Wall’s Brendan Wallace and Hippo’s Assaf Wand discuss proptech’s biggest opportunities — The pair joined us to discuss questions like: How should proptech founders think about competition, strategic investment versus top-tier VC firms and how to build their board?

SaaS subscriptions may be short-serving your customers — Adam Riggs argues that software as a service may have become a bit too interchangeable with subscription models.

(Extra Crunch is our membership program, which helps founders and startup teams get ahead. You can sign up here.)

Everything else

Announcing the Agenda for TC Sessions: Mobility 2021 — Our guests will include Scale AI founder Alexandr Wang, Zoox co-founder and CTO Jesse Levinson, Amy Jones Satrom of Nuro and famed investor Reid Hoffman.

Taking stock of the VC industry’s progress on diversity, equity and inclusion — A look at the VC Human Capital Survey from the National Venture Capital Association, Venture Forward and Deloitte.

The Daily Crunch is TechCrunch’s roundup of our biggest and most important stories. If you’d like to get this delivered to your inbox every day at around 3pm Pacific, you can subscribe here.

Language learning startup Toucan raises $4.5M

Toucan, a startup that helps users learn a new language while they browse the web, is announcing that it has raised an additional $4.5 million in seed funding.

As I wrote last fall, the Santa Monica, Calif.-based startup has built a Chrome extension that scans the text of whatever website you’re reading and translates select words into whichever language you’re trying to learn. That means you’re expanding your vocabulary without having to make time to study or otherwise change your behavior.

Toucan currently supports seven languages — Spanish, Korean, French, German, Italian, Portuguese and Japanese. Co-founder and CEO Taylor Nieman said the company now has around 60,000 monthly active users, all acquired organically.

“On the surface, Toucan can look like a toy, but there’s massive engineering tech on the backend,” Nieman added.

For one thing, although the startup has a team of human translators, it also relies on machine learning and natural language processing to understand the context of each word and make sure it’s being translated properly. Nieman also said that the company also takes an intelligent, personalized approach to the translations that appear over time, allowing them to become more complex in order to keep challenging users.

Toucan screenshot

Image Credits: Toucan

Toucan is free, but users can subscribe to Toucan Premium, which starts at $4.99 per month and offers a higher density of translated words. Premium subscribers can also opt in or out of advertising — apparently the ability to “own” a word (a.k.a. have your sponsorship message appear anytime that word is translated) is popular enough that some paying users don’t want to lose it.

Toucan has now raised a total of $7.5 million. The new round was led by LightShed Ventures, with participation from new investors Next Play Ventures, Concrete Rose Capital, GingerBread Capital, Form Capital, Goodwater Capital, Hampton VC, Spacecadet Ventures, GTMfund, Baron Davis Enterprises and Human Ventures, as well as existing investors GSV Ventures, Amplifyher Ventures and Vitalize.

“Screen time is escalating globally with younger generations living their lives always connected,” said LightShed Ventures General Partner Richard Greenfield in a statement. “Toucan seamlessly integrates language learning into the websites (and soon apps) you are already using via a simple browser extension transforming screen time into learning time.”

Nieman said Toucan will use the new funding to expand the team from 12 to 16. It’s also planning to internationalize — so not just translating English to Spanish, but Spanish to English, and so on — and is launching a new Safari extension (it will support more browsers in the future). The ultimately vision is for Toucan to be “layered wherever you are.”

“We want to be this augmented layer of learning on the web, on mobile browsing, the most popular social apps and even in the physical world,” she said, predicting that in the future, you might be “wearing a crazy cool contact lens that can translate a sign on the subway and provide you with those same micro-moments of learning.”

Property management startup Guesty raises $50M and acquires competitor Your Porter

Guesty, which has created property management software for hosts on short-term rental platforms like Airbnb and Vrbo, is announcing that it has raised $50 million in Series D funding.

“In the public markets, there are many players in hospitality property management,” said co-founder and CEO Amiad Soto. “The same thing goes with residential property management. In short-term rentals, there’s no public player — you can bet your money that we are eyeing that target.”

In the past year, Guesty expanded to support other types of property, including multi-unit listings and “aparthotels.”

And just as Airbnb executives are predicting a travel rebound this year, co-founder and Soto said things are looking pretty good for Guesty’s business; in fact, he predicted that this is going to be “a hell of a year.” For example, summer reservation volume in the United States is 282% higher than in summer 2020, and even 32% higher than summer 2019. In the U.K., summer reservations are up 180% from last year (though down 19% from 2019).

“Yes, the pandemic changed travel, but not necessarily in bad ways across the board,” Soto said. “Definitely for major hotels, there are going to be big changes, but for vacation rentals and boutique-style hotels that offer different experience, this a lot more accessible and a lot more appealing. This is what our investors believe in.”

Guesty has now raised a total of $110 million. The new round was led by Apax Digital Fund with participation from the AMI Opportunities Fund, as well as existing investors Viola Growth, Flashpoint, Vertex Ventures, Kingfisher Investment Advisors and La Maison Partners. Apax Digital Managing Director Daniel O’Keefe is joining Guesty’s board of directors.

“We are incredibly excited to partner with the team at Guesty to help accelerate their mission to bring sophisticated property management solutions to a rapidly shifting global ecosystem,” O’Keefe said in a statement.

Soto added that the money will allow Guesty to continue investing in both growth and technology. For one thing, he said the company already uses machine learning to classify and route 80% of guest messages, and he sees opportunities to expand the use of artificial intelligence in the platform. The startup also plans to continue building out its marketplace of third-party integrations.

And Guesty has been busy on the acquisition front. Earlier this month, it announced acquiring fellow Y Combinator-backed property management platform MyVR, and today it’s revealing that it has also bought another property management company, Your Porter. Soto said that with Your Porter’s technology, Guesty will be able to serve hosts from family-run businesses with a few units to enterprise-scale property management companies.

He added that there will likely be more acquisitions in Guesty’s future: “Instead of all of us duplicating resources, why won’t we share resources […] and create a much broader product?”