The digital transformation currently sweeping society has likely reached your favorite local restaurant.

Since 2013, Boston-based Toast has offered bars and eateries a software platform that lets them manage orders, payments and deliveries.

Over the last year, its customers have processed more than $38 billion in gross payment volume, so Alex Wilhelm analyzed the company’s S-1 for The Exchange with great interest.

“Toast was last valued at just under $5 billion when it last raised, per Crunchbase data,” he writes. “And folks are saying that it could be worth $20 billion in its debut. Does that square with the numbers?”

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Airbnb, DoorDash and Coinbase each debuted at past Y Combinator Demo Days; as of this writing, they employ a combined 10,000 people.

Today and tomorrow, TechCrunch reporters will cover the proceedings at YC’s Summer 20201 Demo Day. In addition to writing up founder pitches, they’ll also rank their favorites.

Even remotely, I can feel a palpable sense of excitement radiating from our team — anything can happen at YC Demo Day, so sign up for Extra Crunch to follow the action.

Thanks very much for reading; I hope you have an excellent week.

Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist

How Amazon EC2 grew from a notion into a foundational element of cloud computing

In August 2006, AWS activated its EC2 cloud-based virtual computer, a milestone in the cloud infrastructure giant’s development.

“You really can’t overstate what Amazon was able to accomplish,” writes enterprise reporter Ron Miller.

In the 15 years since, EC2 has enabled clients of any size to test and run their own applications on AWS’ virtual machines.

To learn more about a fundamental technological shift that “would help fuel a whole generation of startups,” Ron interviewed EC2 VP Dave Brown, who built and led the Amazon EC2 Frontend team.

3 ways to become a better manager in the work-from-home era

Most managers agree that OKRs foster transparency and accountability, but running a team effectively has different challenges when workers are attending all-hands meetings from their kitchen tables.

Instead of just discussing key metrics before board meetings or performance reviews, make them part of the day-to-day culture, recommends Jeremy Epstein, Gtmhub’s CMO.

“Strengthen your team by creating authentic workplace transparency using numbers as a universal language and providing meaning behind your team’s work.”

The pre-pitch: 7 ways to build relationships with VCs

Many founders must overcome a few emotional hurdles before they’re comfortable pitching a potential investor face-to-face.

To alleviate that pressure, Unicorn Capital founder Evan Fisher recommends that entrepreneurs use pre-pitch meetings to build and strengthen relationships before asking for a check:

“This is the ‘we actually aren’t looking for money; we just want to be friends for now’ pitch that gets you on an investor’s radar so that when it’s time to raise your next round, they’ll be far more likely to answer the phone because they actually know who you are.”

Pre-pitches are good for more than curing the jitters: These conversations help founders get a better sense of how VCs think and sometimes lead to serendipitous outcomes.

“Investors are opportunists by necessity,” says Fisher, “so if they like the cut of your business’s jib, you never know — the FOMO might start kicking hard.”

Lessons from COVID: Flexible funding is a must for alternative lenders

FischerJordan’s Deeba Goyal and Archita Bhandari break down the pandemic’s impact on alternative lenders, specifically what they had to do to survive the crisis, taking a look at smaller lenders including Credibly, Kabbage, Kapitus and BlueVine.

“Only those who were able to find a way through the complexities of their existing capital sources were able to maintain their performance, and the rest were left to perish or find new funding avenues,” they write.

Inside Freshworks’ IPO filing

Customer engagement software company Freshworks’ S-1 filing depicts a company that’s experiencing accelerating revenue growth, “a great sign for the health of its business,” reports Alex Wilhelm in this morning’s The Exchange.

“Most companies see their growth rates decline as they scale, as larger denominators make growth in percentage terms more difficult.”

Studying the company’s SEC filing, he found that “Freshworks isn’t a company where we need to cut it lots of slack, as we might with an adjusted EBITDA number. It is going public ready for Big Kid metrics.”

Fifteen years ago this week on August 25, 2006, AWS turned on the very first beta instance of EC2, its cloud-based virtual computers. Today cloud computing, and more specifically infrastructure as a service, is a staple of how businesses use computing, but at that moment it wasn’t a well known or widely understood concept.

The EC in EC2 stands for Elastic Compute, and that name was chosen deliberately. The idea was to provide as much compute power as you needed to do a job, then shut it down when you no longer needed it — making it flexible like an elastic band. The launch of EC2 in beta was preceded by the beta release of S3 storage six months earlier, and both services marked the starting point in AWS’ cloud infrastructure journey.

You really can’t overstate what Amazon was able to accomplish with these moves. It was able to anticipate an entirely different way of computing and create a market and a substantial side business in the process. It took vision to recognize what was coming and the courage to forge ahead and invest the resources necessary to make it happen, something that every business could learn from.

The AWS origin story is complex, but it was about bringing the IT power of the Amazon business to others. Amazon at the time was not the business it is today, but it was still rather substantial and still had to deal with massive fluctuations in traffic such as Black Friday when its website would be flooded with traffic for a short but sustained period of time. While the goal of an e-commerce site, and indeed every business, is attracting as many customers as possible, keeping the site up under such stress takes some doing and Amazon was learning how to do that well.

Those lessons and a desire to bring the company’s internal development processes under control would eventually lead to what we know today as Amazon Web Services, and that side business would help fuel a whole generation of startups. We spoke to Dave Brown, who is VP of EC2 today, and who helped build the first versions of the tech, to find out how this technological shift went down.

Sometimes you get a great notion

The genesis of the idea behind AWS started in the 2000 timeframe when the company began looking at creating a set of services to simplify how they produced software internally. Eventually, they developed a set of foundational services — compute, storage and database — that every developer could tap into.

But the idea of selling that set of services really began to take shape at an executive offsite at Jeff Bezos’ house in 2003. A 2016 TechCrunch article on the origins AWS described how that started to come together:

As the team worked, Jassy recalled, they realized they had also become quite good at running infrastructure services like compute, storage and database (due to those previously articulated internal requirements). What’s more, they had become highly skilled at running reliable, scalable, cost-effective data centers out of need. As a low-margin business like Amazon, they had to be as lean and efficient as possible.

They realized that those skills and abilities could translate into a side business that would eventually become AWS. It would take a while to put these initial ideas into action, but by December 2004, they had opened an engineering office in South Africa to begin building what would become EC2. As Brown explains it, the company was looking to expand outside of Seattle at the time, and Chris Pinkham, who was director in those days, hailed from South Africa and wanted to return home.

Linux is set for a big release this Sunday August 29, setting the stage for enterprise and cloud applications for months to come. The 5.14 kernel update will include security and performance improvements.

A particular area of interest for both enterprise and cloud users is always security and to that end, Linux 5.14 will help with several new capabilities. Mike McGrath, vice president, Linux Engineering at Red Hat told TechCrunch that the kernel update includes a feature known as core scheduling, which is intended to help mitigate processor-level vulnerabilities like Spectre and Meltdown, which first surfaced in 2018. One of the ways that Linux users have had to mitigate those vulnerabilities is by disabling hyper-threading on CPUs and therefore taking a performance hit.

“More specifically, the feature helps to split trusted and untrusted tasks so that they don’t share a core, limiting the overall threat surface while keeping cloud-scale performance relatively unchanged,” McGrath explained.

Another area of security innovation in Linux 5.14 is a feature that has been in development for over a year and a half that will help to protect system memory in a better way than before. Attacks against Linux and other operating systems often target memory as a primary attack surface to exploit. With the new kernel, there is a capability known as memfd_secret () that will enable an application running on a Linux system to create a memory range that is inaccessible to anyone else, including the kernel.

“This means cryptographic keys, sensitive data and other secrets can be stored there to limit exposure to other users or system activities,” McGrath said.

At the heart of the open source Linux operating system that powers much of the cloud and enterprise application delivery is what is known as the Linux kernel. The kernel is the component that provides the core functionality for system operations.

The Linux 5.14 kernel release has gone through seven release candidates over the last two months and benefits from the contributions of 1,650 different developers. Those that contribute to Linux kernel development include individual contributors, as well as large vendors like Intel, AMD, IBM, Oracle and Samsung. One of the largest contributors to any given Linux kernel release is IBM’s Red Hat business unit. IBM acquired Red Hat for $34 billion in a deal that closed in 2019.

“As with pretty much every kernel release, we see some very innovative capabilities in 5.14,” McGrath said.

While Linux 5.14 will be out soon, it often takes time until it is adopted inside of enterprise releases. McGrath said that Linux 5.14 will first appear in Red Hat’s Fedora community Linux distribution and will be a part of the future Red Hat Enterprise Linux 9 release. Gerald Pfeifer, CTO for enterprise Linux vendor SUSE, told TechCrunch that his company’s openSUSE Tumbleweed community release will likely include the Linux 5.14 kernel within “days” of the official release. On the enterprise side, he noted that SUSE Linux Enterprise 15 SP4, due next spring, is scheduled to come with the 5.14 kernel.

The new Linux update follows a major milestone for the open source operating system, as it was 30 years ago this past Wednesday that creator Linus Torvalds (pictured above) first publicly announced the effort. Over that time Linux has gone from being a hobbyist effort to powering the infrastructure of the internet.

McGrath commented that Linux is already the backbone for the modern cloud and Red Hat is also excited about how Linux will be the backbone for edge computing — not just within telecommunications, but broadly across all industries, from manufacturing and healthcare to entertainment and service providers, in the years to come.

The longevity and continued importance of Linux for the next 30 years is assured in Pfeifer’s view. He noted that over the decades Linux and open source have opened up unprecedented potential for innovation, coupled with openness and independence.

“Will Linux, the kernel, still be the leader in 30 years? I don’t know. Will it be relevant? Absolutely,” he said. “Many of the approaches we have created and developed will still be pillars of technological progress 30 years from now. Of that I am certain.”

Embedded fintech company Zeal secured $13 million in Series A funding to continue developing its platform for building individualized payroll products.

Spark Capital led the Series A, with participation from Commerce Ventures and a group of individual investors, including Marqeta CEO Jason Gardner and CRO Omri Dahan, Robinhood founder Vlad Tenev, UltimateSoftware executives Mitch Dauerman and Bob Manne and Namely founder Matt Straz. The latest round now gives the company $14.6 million in total funding, which includes a $1.6 million seed round in 2020, CEO Kirti Shenoy told TechCrunch.

The Bay Area company’s origin was as Puzzl, a payment processing startup for the gig economy, founded in 2018 by Shenoy and CTO Pranab Krishnan. It was part of Y Combinator’s 2019 cohort. The pair had to pivot the company after needing to move some of its thousands of 1099 contractors to W2 employee status.

They went looking for payroll processors that could handle high volumes of payroll automatically, like ADP or Paycor, but found they didn’t match some of the capabilities Shenoy and Krishnan wanted, including to pay workers daily and customize earning components.

To ensure other companies didn’t run into the same problem, they decided to build a payroll API that enables their customers to build their own payroll products, even being able to pay their workers everyday. Traditionally, companies would layer together antiquated third-party payroll tools and spend millions of dollars on consulting fees. Zeal’s API tool modernizes the payroll process and takes on the payroll liability while managing the back-end payment logistics, Shenoy said.

Currently, enterprises use Zeal to pay large volumes of workers and keep payment data on their own native systems, while software platforms that sell business-to-business services use Zeal to build their own payroll product to sell to their customers.

“Our mission is to touch every American paycheck with our tax and payment technology, ensuring that American employees are paid correctly and efficiently,” Krishnan said.

And that is a complex goal: there are 200 million American employees, over $8.8 trillion of payroll is processed annually in the U.S. and the country’s 11,000 tax jurisdictions produce over 25,000 income tax code changes a year.

Meanwhile, Shenoy cited IRS data that showed more than 40% of small and medium businesses pay at least one payroll penalty per year. That was one of the drivers for Zeal’s latest product, the Abacus gross-to-net calculator, which payroll companies can use to ensure they are compliant in paying their income taxes.

The co-founders intend to use the new funding to build out their team and strengthen compliance measures to ensure its track record with enterprises.

“We are starting to win more enterprise deals and moving millions of dollars each day,” Shenoy said. “This has been a legacy space for so long, so companies want to work with a provider to move fast.”

Shenoy predicts that more companies will shift to hyper-customized experiences in the next five to 10 years. Whereas the default was a company like ADP, companies will want to control their own data and build products so their customers can do everything payroll-related from one platform.

As part of the investment, Spark Capital’s partner Natalie Sandman has joined Zeal’s board of directors. The firm previously invested in other embedded fintech companies like Affirm and Marqeta, and she thinks there are new experiences in the sector that APIs can unlock.

Sandman felt the payroll-building pain points herself when she worked at Zenefits. At the time, the company was trying to do the same thing, but there were no APIs to connect with. There were all of these spreadsheets to transfer data, but one wrong deduction would trickle down and cause a tax penalty.

Shenoy and Krishnan are both “customer-obsessed,” she said, and are balancing speed with thoughtfulness when it comes to understanding how their customers want to build payroll products.

She is seeing a macro shift to audience-driven human resources where bringing new employees online will mean embedding them into products that will be more valuable versus the traditional spreadsheet.

“To me, it is a no-brainer that APIs provide flexibility in the way wages and deductions need to be made,” Sandman said. “You can lose trust in your employer. Payroll is at the deepest trust point and where you want transparency and a robust solution to solve that need.”

Stonehenge Technology Labs wants consumer packaged goods companies to gain meaningful use from all of the data they collect. It announced $2 million in seed funding for its STOPWATCH commerce enhancement software.

The round was led by Irish Angels, with participation from Bread and Butter Ventures, Gaingels, Angeles Investors, Bonfire Ventures and Red Tail Venture Capital.

CEO Meagan Kinmonth Bowman founded the Arkansas-based company in 2019 after working at Hallmark, where she was tasked with the digital transformation of the company.

“This was not a consequence of them not being good marketers or connected to mom, but they didn’t have the technology to connect their back end with retailers like Amazon, Walmart or Hobby Lobby,” she told TechCrunch. “There are so many smart people building products to connect with consumers. The challenge is the big guys are doing things the same way and not thinking like the 13-year-olds on social media that are actually winning the space.”

Kinmonth Bowman and her team recognized that there was a missing middle layer connecting the world of dotcom with brick and mortar. If the middle layer could be applied to the enterprise resource plans and integrate public and private data feeds, a company could be just as profitable online as it could be in traditional retail, she said.

Stonehenge’s answer to that is STOPWATCH, which takes in over 100 million rows of data per workspace per day, analyzes the data points, adds real-time alerts and provides the right data to the right people at the right time.

Dan Rossignol, a B2B SaaS investor, said the CPG world is also about consumerizing our life, and the global pandemic showed that even at home, people could have a productive day and business. Rossignol likes to invest in underestimated founders and saw in Stonehenge a company that is getting CPGs out from underneath antiquated technologies.

“What Meagan and her team are doing is really interesting,” he added. “At this stage, it is all about the people, and the ability to bet on doing something larger.”

Kinmonth Bowman said she had the opportunity to base the company in Silicon Valley, but chose Bentonville, Arkansas instead to be closer to the more than 1,000 CPG companies based there that she felt were the prime customer base for STOPWATCH.

The platform was originally created as a subsidiary of a consulting company, but in 2018, one of their clients told them they just wanted the software rather than also paying for the consulting piece. The business was split, and Stonehenge went underground for eight months to make a software product specifically for the client.

Kinmonth Bowman admits the technology itself is not that sexy — it is using exact transfer loads to extract data from hundreds of systems into a “lake house,” and then siloing it by retailer and other factors and then presenting the data in different ways. For example, the CEO will want different metrics than product teams.

Over the past year, the company has doubled its revenue and also doubled the amount of contracts. It already counts multiple Fortune 100 companies and emerging brands as some of its early users and plans to use the new funding to hire a sales team and go after some strategic relationships.

Stonehenge is also working on putting together a diverse workforce that mimics the users of the software, Kinmonth Bowman said. One of the challenges has been to get unique talent to move to Arkansas, but she said it is one she is eager to take on.

Meanwhile, Brett Brohl, managing partner at Bread and Butter Ventures, said the Stonehenge team “is just crazy enough, smart and driven” to build something great.

“All of the biggest companies have been around for a long time, but not a lot of large organizations have done a good job digitizing their businesses,” he said. “Even pre-COVID, they were building fill-in-the-blank digital transformations, but COVID accelerated technology and hit a lot of companies in the face. That was made more obvious to end consumers, which puts more pressure on companies to understand the need, which is good for STOPWATCH. It went from paper to Excel spreadsheets to the next cloud modification. The time is right for the next leap and how to use data.”