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A recapitalization reckoning

If you’re an angel who invested in a startup that was meant to go public in 2014, you might be getting a little bit impatient. High-risk, high-reward investing has lost its shine in this environment: the stock market is a mess these days, and you want your cash back.

Enter recapitalization events, where startups restructure their entire cap table to squeeze out old investors, bring on new ones and shift the way equity and debt is managed. For investors, it’s a killer way to enter a company on friendlier terms than normal (read: desperation), and a nice way to get liquidity on a startup you’re betting on.

For founders, it’s rarely good news, as departing investors is not a metric they’re going to add to the pitch deck. As one investor said on background, the spur of coronavirus-related recapitalization events shows “hella dilution for desperate times.”

That’s what makes Workhuman’s transparency with its recent recapitalization event all the more enticing.

Last year, the human-resources platform brought in $580 million in revenue from customers like LinkedIn, Cisco, J&J and other clients. In April, business grew 40%. Co-founder and CEO Eric Mosley says business has grown five times in size since the company pulled back from its 2014 plans to IPO. Workhuman hasn’t raised a single venture round since 2004 (and doesn’t plan to any time soon).

Being conservative has paid off; although Workhuman has operated for nearly two decades, Mosley says he thinks the company is still at the “tip of the iceberg.” The company recently had a recapitalization event to sell the stakes of its earliest investors, who cut a $200,000 check more than 20 years ago.

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Rackspace preps IPO after going private in 2016 for $4.3B

After going private in 2016 after accepting a $32 per share, or $4.3 billion, price from Apollo Global Management, Rackspace is looking once again to the public markets. First going public in 2008, Rackspace is taking second aim at a public offering around 12 years after its initial debut.

The company describes its business as a “multicloud technology services” vendor, helping its customers “design, build and operate” cloud environments. That Rackspace is highlighting a services focus is useful context to understand its financial profile, as we’ll see in a moment.

But first, some basics. The company’s S-1 filing denotes a $100 million placeholder figure for how much the company may raise in its public offering. That figure will change, but does tell us that firm is likely to target a share sale that will net it closer to $100 million than $500 million, another popular placeholder figure.

Rackspace will list on the Nasdaq with the ticker symbol “RXT.” Goldman, Citi, J.P. Morgan, RBC Capital Markets and other banks are helping underwrite its (second) debut.

Financial performance

Similar to other companies that went private, only later to debut once again as a public company, Rackspace has oceans of debt.

The company’s balance sheet reported cash and equivalents of $125.2 million as of March 31, 2020. On the other side of the ledger, Rackspace has debts of $3.99 billion, made up of a $2.82 billion term loan facility, and $1.12 billion in senior notes that cost the firm an 8.625% coupon, among other debts. The term loan costs a lower 4% rate, and stems from the initial transaction to take Rackspace private ($2 billion), and another $800 million that was later taken on “in connection with the Datapipe Acquisition.”

The senior notes, originally worth a total of $1,200 million or $1.20 billion, also came from the acquisition of the company during its 2016 transaction; private equity’s ability to buy companies with borrowed money, later taking them public again and using those proceeds to limit the resulting debt profile while maintaining financial control is lucrative, if a bit cheeky.

Rackspace intends to use IPO proceeds to lower its debt-load, including both its term loan and senior notes. Precisely how much Rackspace can put against its debts will depend on its IPO pricing.

Those debts take a company that is comfortably profitable on an operating basis and make it deeply unprofitable on a net basis. Observe:

Image Credits: SEC

Looking at the far-right column, we can see a company with material revenues, though slim gross margins for a putatively tech company. It generated $21.5 million in Q1 2020 operating profit from its $652.7 million in revenue from the quarter. However, interest expenses of $72 million in the quarter helped lead Rackspace to a deep $48.2 million net loss.

Not all is lost, however, as Rackspace does have positive operating cash flow in the same three-month period. Still, the company’s multi-billion-dollar debt load is still steep, and burdensome.

Returning to our discussion of Rackspace’s business, recall that it said that it sells “multicloud technology services,” which tells us that its gross margins will be service-focused, which is to say that they won’t be software-level. And they are not. In Q1 2020 Rackspace had gross margins of 38.2%, down from 41.3% in the year-ago Q1. That trend is worrisome.

The company’s growth profile is also slightly uneven. From 2017 to 2018, Rackspace saw its revenue expand from $2.14 billion to $2.45 billion, growth of 14.4%. The company shrank slightly in 2019, falling from $2.45 billion in revenue in 2018 to $2.44 billion the next year. Given the economy that year, and the importance of cloud in 2019, the results are a little surprising.

Rackspace did grow in Q1 2020, however. The firm’s $652.7 million in first-quarter top-line easily bested in its Q1 2019 result of $606.9 million. The company grew 7.6% in Q1 2020. That’s not much, especially during a period in which its gross margins eroded, but the return-to-growth is likely welcome all the same.

TechCrunch did not see Q2 2020 results in its S-1 today while reading the document, so we presume that the firm will re-file shortly to include more recent financial results; it would be hard for the company to debut at an attractive price in the COVID-19 era without sharing Q2 figures, we reckon.

How to value Rackspace is a puzzle. The company is tech-ish, which means it will find some interest. But its slow growth rate, heavy debts and lackluster margins make it hard to pin a fair multiple onto. More when we have it.

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Operator Collective brings diversity and inclusion to enterprise investing

When Mallun Yen started Operator Collective last year, she wanted to build an investment firm for people who didn’t have a voice in Silicon Valley. That meant connecting women and people of color with operators who have been intimately involved in building companies from the ground up, then providing early-stage investment.

She then brought in Leyla Seka as a partner. Seka helped build the AppExchange at Salesforce into a powerful marketplace for companies built on top of the Salesforce platform, or that plugged into the platform in some meaningful way to sell their offerings directly to Salesforce customers. Through that role, she met a lot of people in the startup world, and she saw a lot of inequities.

Yen, whose background includes eight years as a VP at Cisco, and co-founder of Saastr with Jason Lemkin, wanted to build a different kind of firm, one that connected these operators — women like herself and Seka, who had walked the walk of running substantial businesses — with people who didn’t typically get heard in the corridors of VC firms.

Those operators themselves tend to be underrepresented at investment shops. The firm today consists of 130 operator LPs, 90% of whom are women and 40% people of color (which includes Asians). One way that the company can do this is by removing rigid buy-in requirements. LPs can contribute as little as $10,000, all the way up to millions of dollars, depending on their means, and that makes for a much more diverse pool of LPs.

While Seka admits they are far from perfect, she says they are fighting the good fight. So far, the company has invested in 18 startups with a more diverse set of founders and executives than you find at most firms that invest in enterprise startups. That means that 67% of their investments include people of color (which breaks down to 44% Asian, 17% Latinx and 6% Black), 56% include a female founder, 56% have an immigrant founder and 33% have a female CEO.

I sat down with Yen and Seka to discuss their thinking about enterprise investing. While they have a far more inclusive philosophy than most, their general approach to enterprise investing isn’t all that different than what we’ve seen in previous surveys with enterprise investors.

Which trends are you most excited about in the enterprise from an investing perspective?

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What do investors bidding up tech shares know that the rest of us don’t?

The biggest story to come out of the post-March stock market boom has been explosive growth in the value of technology shares. Software companies in particular have seen their fortunes recover; since March lows, public software companies’ valuations have more than doubled, according to one basket of SaaS and cloud stocks compiled by a Silicon Valley venture capital firm.

Such gains are good news for startups of all sizes. For later-stage upstarts, software share appreciation helps provide a welcoming public market for exits. And, strong public valuations can help guide private dollars into related startups, keeping the capital flowing.


The Exchange explores startups, markets and money. You can read it every morning on Extra Crunch, and now you can receive it in your inbox. Sign up for The Exchange newsletter, which drops every Friday starting July 24.


For software-focused startup companies, especially those pursuing recurring revenue models like SaaS, it’s a surprisingly good time to be alive.

Indeed, after COVID-19 hit the United States, layoffs and rising software sales churn were key, worrying indicators coming out of startup-land. Since then, the data has turned around.

As TechCrunch reported in June, startup layoffs have declined and software churn has recovered to the point that business and enterprise-focused SaaS companies are on the bounce.

But instead of merely recovering to near pre-COVID levels, software stocks have continued to rise. Indeed, the Bessemer Cloud Index (EMCLOUD), which tracks SaaS firms, has set an array of all-time highs in recent weeks.

There’s some logic to the rally. After speaking to venture capitalists over the past few weeks, notes from EQT VenturesAlastair Mitchell, Sapphire’s Jai Das, and Shomik Ghosh from Boldstart Ventures paint the picture of a possibly accelerating digital transformation for some software companies, nudged forward by COVID-19 and its related impacts.

The result of the trend may be that the total addressable market (TAM) for software itself is larger than previously anticipated. Larger TAM could mean bigger future sales for and more substantial future cash flows for some software companies. This argument helps explain part of the market’s present-day enthusiasm for public tech equities, and especially the shares of software companies.

We won’t be able explain every point that Nasdaq has gained. But the TAM argument is worth understanding if we want to grok a good portion of the optimism that is helping drive tech valuations, both private and public.

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Daily Crunch: Apple releases public beta of iOS 14

A beta version of Apple’s latest mobile operating system is available to the public, Coinbase may go public and researchers discover a frightening smartwatch vulnerability. Here’s your Daily Crunch for July 9, 2020.

The big story: Apple releases public beta of iOS 14

Developers are no longer the only ones who can try out the newest version of Apple’s mobile operating system — beta versions of iOS 14 and iPadOS 14 are now available to the general public.

Romain Dillet has already been playing around with the new iOS, and he said the biggest change is a rethinking of the home screen, with widgets that can be stacked and flipped, along with an App Library that groups all the apps on your phone by category.

The tech giants

WhatsApp Business, now with 50M MAUs, adds QR codes and catalog sharing — The Facebook-owned messaging app is introducing new tools for businesses to connect digitally with their customers.

Apple says it’s ‘committed’ to supporting Thunderbolt on new Macs after Intel details latest version — “We remain committed to the future of Thunderbolt and will support it in Macs with Apple silicon,” Apple said.

Amazon’s Alexa heads Toni Reid and Rohit Prasad are coming to Disrupt — Two of the main executives behind Amazon’s leading smart assistant are coming to Disrupt 2020, which will run (virtually) from September 14 to 18.

Startups, funding and venture capital

Coinbase reported to consider late 2020, early 2021 public debut — The cryptocurrency exchange platform may be considering a direct listing instead of a traditional IPO, according to Reuters.

Kernel raises $53 million for its non-invasive ‘Neuroscience as a Service’ technology — The startup says it has created non-invasive technology for recording brain activity.

TikTok likes and views are broken as community worries over potential US ban — As of this afternoon, the company said a fix was in progress.

Advice and analysis from Extra Crunch

VCs are cutting checks remotely, but deal volume could be slowing — In a new survey from OMERS Ventures, 69% of VCs said they were willing to make a fully remote investment, but most of them haven’t actually done so.

As the pandemic drags on, interest in automation surges — Brian Heater looks at some of the ways COVID-19 may permanently alter the job market.

K Fund’s Jaime Novoa discusses early-stage firm’s focus on Spanish startups — The firm officially unveiled its €70 million second fund earlier this month.

(Reminder: Extra Crunch is our subscription membership program, which aims to democratize information about startups. You can sign up here.)

Everything else

Smartwatch hack could trick patients to ‘take pills’ with spoofed alerts — The vulnerabilities were found in SETracker, a cloud system that powers smartwatches and vehicles.

Coronavirus impact sends app downloads, usage and consumer spending to record highs in Q2 — Mobile app usage grew 40% year-over-year, according to App Annie.

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.

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iOS 14 gets rid of the app grid to help you find the app you’re looking for

Apple unveiled the next major version of iOS a few weeks ago. I’ve been playing around with beta versions of iOS 14 and here’s what you should expect when you update your iPhone to the final release of iOS 14 this fall.

The most interesting change is something you’re not going to notice at first. The home screen has been rethought. In some ways, the iPhone now works more like Android devices. You can add widgets to the home screen and there’s a new app launcher called the App Library.

If you’ve been using a smartphone for many years, chances are your device is cluttered with a dozen apps you frequently use, some apps you only need a few times a year and a ton of apps that are no longer useful.

Maybe your home screen is perfectly organized and you’re thinking that this doesn’t apply to you. Arguably, you’re part of the minority. Many people tell me they don’t even know where app icons are located anymore and they just pull down to use the search feature.

With iOS 14, changes are not immediately visible. If you want to keep using your phone just like before, nobody is stopping you. But the home screen is now more customizable.

Image Credits: Apple

When you tap and hold on a home screen icon, there’s a new menu that lists all the widgets you can install on your home screen. Many default apps already support widgets, such as Reminders, Calendar, Stock, Weather, Music, etc. And each widget comes in multiple sizes if you want to see more or less info.

The most interesting thing about widgets is that you can stack them and flip through them. Otherwise, they’d quickly take over your entire home screen. Apple also tries to surface the widget that is more relevant to the time of the day and what you’re doing.

The second big change with the home screen is that there’s a new page at the right of your last page. The App Library groups all your apps on your phone by category. Some icons are bigger than others as Apple tries once again to surface the most important apps to you.

In my experience, categories don’t work that well as they’re based on the broad categories of the App Store. But you can always tap on the search bar at the top to display an alphabetical list of your apps. It could be useful if you can’t remember the name of an app, for instance.

Image Credits: Apple

Fighting app fatigue

Those changes for the home screen might seem minor, but they are important to change the current app paradigm. People simply don’t want to download new apps. They don’t want to create a new account and they don’t want to have another icon.

Now that you can hide pages of apps and that there’s the App Library, downloading new apps has become less intimidating. If you combine that with Sign in with Apple, you can go from no app to interacting with content in no time.

In addition to that, Apple is introducing App Clips. They are sort of mini apps that you can launch without installing an app. It’s a small part of an app that you can easily share. I haven’t had the chance to try it out yet as third-party developers have yet to take advantage of App Clips.

There are many ways to share App Clips. You can launch those apps from the web, from Messages, from Maps, from NFC tags or from QR codes. Get ready to see stickers at cafés, on scooters or in museums. Scan a code or tap your phone on it and you get an app-like experience. If you want to dive deeper, you can download the full app from the App Library.

But it’s also going to have some major impacts on utility apps, apps that you don’t use that often or travel apps for instance. Sure, you may keep your favorite social app on your home screen. But you’re going to forget about apps that only live in the App Library.

Developers will be happy that downloading apps is easier. And yet, it is going to be harder to make people come back to your app after the first launch.

Image Credits: Apple

Some app refinements

Let me list some quality-of-life improvements that are going to make your phone work better. In Messages, you can now pin conversations to the top. Group conversations are also receiving a major update with the ability to @-mention people, reply to specific messages and set a group of photos. Once again, Apple is bringing Messages closer to WhatsApp and Telegram. But it’s not a bad thing.

In Maps, there are many new features that I already detailed in a separate post. I encourage you to read it if you want to learn more about guides, electric vehicle routing, cycling directions and more.

The Home app has been improved with a new row of icons that describe the status of your home. For instance, you can see the temperature, see if a door is open, see if lights are on, etc.

Like every year, Notes and Reminders are getting some small improvements. For instance, document scanning has been improved, search has been improved, you can assign reminders to others and more. Those apps have become really powerful with these small incremental updates.

Image Credits: Apple

All the rest

There are many things that I haven’t mentioned yet or that I haven’t tried because I can’t use those features yet. Similarly, it’ll take some time before developers start adopting those features. Here’s a quick rundown:

  • Incoming calls don’t take over the entire screen anymore. You get a notification at the top of the screen, which is so much better if you don’t want to answer a call.
  • Similarly, Siri doesn’t overtake the screen. Your display fades out. I think more people are going to use Siri because of this as it doesn’t feel as invasive.
  • Your AirPods will automatically switch between your iPhone, iPad, Mac, etc.
  • When you’re on a FaceTime call or watching a video, you can switch to another app and keep the video in a corner. There’s not much else to say other than it’s nice.
  • Cycling directions in Apple Maps: I’m a bike lover, but the feature isn’t available in Paris. It’s hard to know whether directions make sense in San Francisco or New York as I don’t know cycling infrastructure that well in those cities.
  • When you pull down to search for something, iOS now automatically highlights the first result. You can tap Go on the keyboard to hit the first result. It’s so much better.
  • HomeKit-compatible security cameras can now recognize faces based on tags in Photos.
  • You can unlock cars with your phone using NFC if you have a compatible car.
  • Following the acquisition of Dark Sky, you’ll be able to see next-hour precipitation in Apple’s Weather app.
  • You’ll be able to choose a different web browser and email client as default apps with iOS 14.

What about stability?

The big issue of iOS 13 was that it was quite buggy when it launched in September 2019. It’s hard to know whether iOS 14 is going to perform better on this front as it’s still a beta.

But, as you can see, Apple didn’t try to reinvent the wheel with default apps. There are a ton of improvements across the board, but no big redesign of Photos or Messages for instance. And I think it’s a good thing.

Changes on the home screen as well as App Clips could have wider implications for developers. It could change the way you discover and install apps today. So it’s going to be interesting to see if the developer community embraces App Clips.

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Apple just released the first iOS 14 beta to everyone

This is your opportunity to get a glimpse of the future of iOS — and iPadOS. Apple just released the first public beta of iOS 14 and iPadOS 14, the next major version of the operating systems for the iPhone and iPad. Unlike developer betas, everyone can download these betas without a $99 developer account. But don’t forget, it’s a beta.

The company still plans to release the final version of iOS and iPadOS 14.0 this fall. But Apple is going to release betas every few weeks over the summer. It’s a good way to fix as many bugs as possible and gather data from a large group of users.

As always, Apple’s public betas closely follow the release cycle of developer betas. And Apple released the second developer beta of iOS and iPadOS 14 earlier this week. So it sounds like the first public beta is more or less the same build as the second developer build.

But remember, you shouldn’t install an iOS beta on your primary iPhone or iPad. The issue is not just bugs — some apps and features won’t work at all. In some rare cases, beta software can also brick your device and make it unusable. You may even lose data on iCloud. Proceed with extreme caution.

But if you have an iPad or iPhone you don’t need, here’s how to download it. Head over to Apple’s beta website and download the configuration profile. It’s a tiny file that tells your iPhone or iPad to update to public betas like it’s a normal software update.

You can either download the configuration profile from Safari on your iOS device directly, or transfer it to your device using AirDrop, for instance. Reboot your device, then head over to the Settings app. In September, your device should automatically update to the final version of iOS and iPadOS 13 and you’ll be able to delete the configuration profile.

The biggest change of iOS 14 is the introduction of widgets on the home screen, a new App Library to browse all your apps and the ability to run App Clips — those are mini apps that feature a small part of an app and that you can run without installing anything.

There are also many refinements across the board, such as new features for Messages, with a big focus on groups with @-mentions and replies, a new Translate app that works on your device, cycling directions in Apple Maps in some cities and various improvements in Notes, Reminders, Weather, Home and more.

If you want to learn more about iOS 14, I looked at some of the features in the new version:

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K Fund’s Jaime Novoa discusses early-stage firm’s focus on Spanish startups

Earlier this month, Spanish early-stage venture capital firm K Fund officially launched its second fund, which sits at €70 million, up from €50 million the first time around.

Targeting Spanish startups with an international outlook, the seed-stage firm plans to invest from €200,000 to €2 million, writing first checks in 25-30 companies. Meanwhile, a portion of the fund will also be set aside for follow-on funding for the most promising of its portfolio.

Described as business model- and sector-agnostic, K Fund currently has a mix of B2B and B2C companies in its portfolio across a wide variety of sectors, such as travel, fintech, insurtech and others. They include online travel agency Exoticca, HR software Factorial, insurtech startup Bdeo and Hubtype, a conversational messaging tech provider.

I caught up with K Fund’s Jaime Novoa to delve deeper into the firm’s investment remit, how the Spanish startup and tech ecosystem has developed over the last few years and to learn more about “K Founders,” the VC’s new pre-seed funding program.

TechCrunch: K Fund’s first fund was announced in late 2016 to back startups in Spain with an international outlook at seed and Series A. At €70 million, this second fund is €20 million larger but I gather the remit remains broadly the same. Can you be more specific with regards to cheque size, geography, sector and the types of startups you look for?

Jaime Novoa: We’re both agnostic in terms of business models and industries. Since our focus is, for the most part, Spain, we do not believe that the Spanish market is big enough to build a vertically focused fund, either in terms of business model or sector.

With our first fund we invested in 28 companies, with a slightly larger number of B2B SaaS companies than B2C ones, and across a wide variety of sectors. We do have a bit of exposure to travel and fintech/insurtech, but that’s because we’ve found several interesting companies in those spaces, not because we proactively said, “let’s invest in fintech/travel.”

In terms of check sizes, the core of the fund will be to make the same type of investments as in our first fund: first cheques from €200k to €2m and then sufficient capital for follow-on rounds. We’ll probably do a similar number of deals compared to the previous fund, but we want to have additional capital for follow-on purposes.

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Docker partners with AWS to improve container workflows

Docker and AWS today announced a new collaboration that introduces a deep integration between Docker’s Compose and Desktop developer tools and AWS’s Elastic Container Service (ECS) and ECS on AWS Fargate. Previously, the two companies note, the workflow to take Compose files and run them on ECS was often challenging for developers. Now, the two companies simplified this process to make switching between running containers locally and on ECS far easier.

docker/AWS architecture overview“With a large number of containers being built using Docker, we’re very excited to work with Docker to simplify the developer’s experience of building and deploying containerized applications to AWS,” said Deepak Singh, the VP for compute services at AWS. “Now customers can easily deploy their containerized applications from their local Docker environment straight to Amazon ECS. This accelerated path to modern application development and deployment allows customers to focus more effort on the unique value of their applications, and less time on figuring out how to deploy to the cloud.”

In a bit of a surprise move, Docker last year sold off its enterprise business to Mirantis to solely focus on cloud-native developer experiences.

“In November, we separated the enterprise business, which was very much focused on operations, CXOs and a direct sales model, and we sold that business to Mirantis,” Docker CEO Scott Johnston told TechCrunch’s Ron Miller earlier this year. “At that point, we decided to focus the remaining business back on developers, which was really Docker’s purpose back in 2013 and 2014.”

Today’s move is an example of this new focus, given that the workflow issues this partnership addresses had been around for quite a while already.

It’s worth noting that Docker also recently engaged in a strategic partnership with Microsoft to integrate the Docker developer experience with Azure’s Container Instances.

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Creandum backs Amie, a new productivity app from ex-N26 product manager Dennis Müller

Amie, a new productivity app from ex-N26 product manager Dennis Müller, has picked up $1.3 million in pre-seed funding to “kickstart” development and hiring.

Backing 23-year-old Müller is Creandum — the European VC best known for being an early investor in Spotify — along with Tiny.VC and a plethora of angels. They include Laura Grimmelmann (Ex-Accel), Nicolas Kopp (CEO, N26 U.S.), Roland Grenke (Dubsmash co-founder) and Zachary Smith (SVP of product at U.S. challenger bank Chime).

Founded early this year and with a planned launch in early 2021, Berlin-based Amie is developing a productivity app that combines a person’s calendar and to-dos in one place. Previously called coco, it promises to work across all devices, with an interface that “works just like you think.”

“Back in the day, you had a calendar on your office wall, and a to-do list on a notepad,” Müller tells me. “You could take your list with you elsewhere, but not your calendar. Those were digitized instead of rethinking the flow. Most productivity apps solve very specific problems, creating a new one, [and] users need too many tools.”

Amie pre-release app screenshot.

Müller says Amie is built on the principle that “to-dos, habits and events all take time, and all belong in the same place.” Many people already schedule to-dos and the startup wants to offer the fastest way to create to-dos, schedule events, check your calendar “and even jump into Zoom calls.”

As a glimpse of what’s to come, Amie promises to let you drag ‘n’ drop to-dos into your day, or turn links and screenshots into to-dos. “With Amie’s Alfred-like app, you can create an event and invite people in a different timezone, all while other apps are still loading,” says the young company.

More broadly, Amie wants to act as a central workspace, letting you also do things like join video calls, take notes and do email, without the need to open extra browser tabs and therefore avoid “context switching.”

“Amie will target professionals who are currently using Google Calendar, due to our integration,” adds Müller. “The waitlist already counts thousands of users, who are mostly professionals working in the tech industry (e.g., designers, developers, bizdevs, etc.”

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