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Booming edtech M&A activity brings consolidation to a fragmented sector

As the COVID-19 pandemic continues to force teachers, students and parents to adopt new technologies, edtech’s total addressable market has massively grown in the last several months. The shift has urged venture capitalists to pour money into the sector accordingly, ushering a number of startups into the unicorn club.

But maturation doesn’t just mean bigger checks and high-flying unicorns — it also brings exits.

Edtech M&A activity is buzzier than usual: In the last week, Course Hero, a startup that sells Netflix-like subscriptions to students looking for learning and teaching content, bought Symbolab, an artificial intelligence-powered calculator. Saga Education, a tutoring nonprofit backed by Comcast, the Bill & Melinda Gates Foundation and others, acquired math software platform Woot Math. We also saw PowerSchool, which sells a suite of software services to manage schools, scoop up Hoonuit, a data management and analytics tool for educators. Finally, K-12 curriculum company Discovery Education bought K-5 science and stem curriculum upstart Mystery Science.

It’s a lot of news in a short period of time. Luckily, these consolidations offer some directional guidance regarding where some edtech businesses think the future of their industry is headed.

Smart content as a competitive advantage

Content, to an extent, is commoditized. If you can find a free tutorial on Youtube or Khan Academy, buy a subscription to an edtech platform that offers the same solution? The commodification of education is good for end-users and is often why startups have a freemium model as a customer acquisition strategy. To convert free users into paying subscribers, edtech startups need to offer differentiated and targeted content.

The Course Hero and Mystery Science deals show us that edtech businesses are hungry for personalized, targeted content. Course Hero’s acquisition of Symbolab was essentially a deal for more than a decade’s worth of data that captured which math questions students found hardest.

Symbolab is a math calculator that is set to answer over 1 billion questions this year. With each answer, Symbolab adds information to its algorithm regarding students’ most common pain points and confusion. Course Hero, in contrast, is a broader service that focuses on Q&A from a variety of subjects. CEO Andrew Grauer says Symbolab’s algorithm isn’t something that Course Hero, which has been operating since 2006, can drum up overnight. That’s precisely why he “decided to buy, instead of build.”

“It made a lot of sense to move fast enough so it wouldn’t take up multiple years to get this technology,” Grauer said. The deal was made as big companies get in the Q&A game too, he noted. Google acquired homework helper app Socratic in 2019 and Microsoft built Microsoft Solver in the same year.

Discovery Education, a curriculum provider for K-12 classrooms, acquired San Francisco-based K-5 STEM curriculum provider, Mystery Science. Discovery Education has launched a series of other products focused on science education, including Discovery Education Experience, the Science Techbook series and STEM Connect.  However, Mystery Science is largely focused on offering a creative digital solution to science education. The programming, a mix of videos, prompts and projects, cover a range of questions such as, “Where do rivers flow?” and “Could a volcano pop up where you live?” for young students.

Mystery Science CEO and founder Keith Schact explained how his product focuses on kids and educators, while Discovery Education focuses on educators and districts, making the deal feel like a “natural marriage.” Even as edtech goes directly to consumers, Schact remains bullish on the role that institutions play in true adoption of technology.

“You can go straight to teachers and get a certain market share,” he said. “But the institutions still do have a big role.” The founder likened the dynamic to the state of media: With the rise of blogs, you can publish directly and reach an engaged audience, but writers who want a bigger positioning tend to join larger platforms to grow their overall reach. Edtech is the same, in that some startups need an official sign-off from schools before they can reach venture-scale returns.

According to a source familiar with the transaction, Mystery Science was sold for $175 million after only raising $4 million in venture financing.

Using data management and analytics to improve student outcomes

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Coupa Software snags Llamasoft for $1.5B to bring together spending and supply chain data

Coupa Software, a publicly traded company that helps large corporations manage spending, announced that it was buying Llamasoft, an 18-year-old Michigan company that helps large companies manage their supply chain. The deal was pegged at $1.5 billion.

This year Llamasoft released its latest tool, an AI-driven platform for managing supply chains intelligently. This capability in particular seemed to attract Coupa’s attention, as it was looking for a supply chain application to complement its spend management capabilities.

Coupa CEO and chairman Rob Bernshteyn says when you combine that supply chain data with Coupa’s spending data, it can produce a powerful combination.

“Llamasoft’s deep supply chain expertise and sophisticated data science and modeling capabilities, combined with the roughly $2 trillion of cumulative transactional spend data we have in Coupa, will empower businesses with the intelligence needed to pivot on a dime,” Bernshteyn said in a statement.

The purchase comes at a time when companies are focusing more and more on digitizing processes across enterprise, and when supply chains can be uncertain, depending on the location of COVID hotspots at any particular time.

“With demand uncertainty on one hand, and supply volatility on the other, companies are in need of supply chain technology that can help them assess alternatives and balance trade-offs to achieve desired business results. LLamasoft provides these capabilities with an AI-powered cloud platform that empowers companies to make smarter supply chain decisions, faster,” the company wrote in a statement.

Llamasoft was founded in 2002 in Ann Arbor, Michigan and has raised more than $56 million, according to Crunchbase data. Its largest raise was a $50 million Series B in 2015 led by Goldman Sachs .

The company generated more than $100 million in revenue and has 650 big customers, including Boeing, DHL, Kimberly-Clark and GM, according to company data.

Coupa has been extremely acquisitive over the years, buying 17 companies, according to Crunchbase data. This deal represents the fourth acquisition this year for the company. So far the stock market is not enamored with the acquisition; the company’s stock price is down 5.20% at publication.

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Twilio wraps $3.2B purchase of Segment after warp-speed courtship

It was barely a month ago we began hearing rumors that Twilio was interested in acquiring Segment. The $3.2 billion deal was officially announced three weeks ago, and this morning the communications API company announced that the deal had closed, astonishingly fast for an acquisition of this size.

While we can’t know for sure, the speed with which the deal closed could suggest that it was in the works longer than we had known, and when we began hearing rumors of the acquisition, it could have already been signed, sealed and delivered. In addition, the fact that Twilio CEO Jeff Lawson and Segment CEO Peter Reinhardt knew one another before coming to terms might have helped accelerate the process.

Regardless, the two companies are a nice fit. Both deal with the API economy, providing a set of tools to help developers easily add a particular set of functions to their applications. For Twilio, that’s a set of communications APIs, while Segment focuses on customer data.

When you pull the two sets of tooling together, and combine that with Twilio’s 2018 SendGrid acquisition, you can see the possibility to build more complete applications for interacting with customers at every level, including basic communications like video, SMS and audio from Twilio, as well as customer data from Segment and customized emails and ads based on those interactions from SendGrid.

As companies increasingly focus on digital engagement, especially in the midst of a pandemic, Twilio’s Lawson believes the biggest roadblock to this type of engagement has been that data has been locked in silos, precisely the kind of problem that Segment has been attacking.

“With the addition of Segment, Twilio’s Customer Engagement Platform now enables companies to both understand their customer and engage with them digitally — the combination is key to building great digital experiences,” Lawson said in a statement.

In a recent post looking at the reasoning behind the deal, Brent Leary, founder and principal analyst at CRM Essentials, saw it this way: “This move allows Twilio to impact the data-insight-interaction-experience transformation process by removing friction from developers using their platform,” Leary explained.

With the deal closed, Segment will become a division of Twilio. Reinhardt will continue to be CEO, and will report directly to Lawson.

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Email creation startup Stensul raises $16M

Stensul, a startup aiming to streamline the process of building marketing emails, has raised $16 million in Series B funding.

When the company raised its $7 million Series A two years ago, founder and CEO Noah Dinkin told me about how it spun out of his previous startup, FanBridge. And while there are many products focused on email delivery, he said Stensul is focused on the email creation process.

Dinkin made many similar points when we discussed the Series B last week. He said that for many teams, creating a marketing email can take weeks. With Stensul, that process can be reduced to just two hours, with marketers able to create the email on their own, without asking developers for help. Things like brand guidelines are already built in, and it’s easy to get feedback and approval from executives and other teams.

Dinkin also noted that while the big marketing clouds all include “some kind of email builder, it’s not their center of gravity.”

He added, “What we tell folks [is that] literally over half the company is engineers, and they are only working on email creation.”

Stensul

Image Credits: Stensul

The team has recently grown to more than 100 employees, with new customers like Capital One, ASICS Digital, Greenhouse, Samsung, AppDynamics, Kroger and Clover Health. New features include an integration with work management platform Workfront.

Plus, with other marketing channels paused or diminished during the pandemic, Dinkin said that email has only become more important, with the old, time-intensive process becoming more and more of a burden.

“We need more emails — whether that’s more versions or more segments or more languages, the requests are through the roof,” he said. “The teams are the same size … and so that’s where especially the leaders of these organizations have looked inward a lot more. The ways that they have been doing it for years or decades just doesn’t work anymore and prevents them from being competitive in the marketplace.”

The new round was led by USVP, with participation from Capital One Ventures, Peak State Ventures, plus existing investors Javelin Venture Partners, Uncork Capital, First Round Capital and Lowercase Capital . Individual investors include Okta co-founder and COO Frederic Kerrest, Okta CMO Ryan Carlson, former Marketo/Adobe executive Aaron Bird, Avid Larizadeh Duggan, Gary Swart and Talend CMO Lauren Vaccarello.

Dinkin said the money will allow Stensul to expand its marketing, product, engineering and sales teams.

“We originally thought: Everybody who sends email should have an email creation platform,” he said. “And ‘everyone who sends email’ is synonymous with ‘every company in the world.’ We’ve just seen that accelerate in that last few years.”

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Leena AI nabs $8M Series A as it expands from chatbots to HR service platform

When we covered Leena AI as a member of the Y Combinator Summer 2018 cohort, the young startup was firmly focused on building HR chatbots, but in the intervening years it has expanded the vision to a broader HR policy platform. Today, the company announced an $8 million Series A led by Greycroft with help from several individual industry investors.

Company CEO and co-founder Adit Jain says that in 2018 the company was concentrating on building an intelligent virtual assistant for HR-related questions. It allowed employees to ask the bot questions like how many vacation days they have left or what holidays they have off this year.

Over the last couple of years since leaving Y Combinator, the company has moved into broader HR service delivery. “So I’m talking about having an intelligent case management, knowledge management and document management system, which is backing the virtual assistant as well,” Jain explained.

He says that users should think of it as an entire system where the chatbot is the user interface for employees to interact with the HR information on the back end. For example, he says that the knowledge management component is where the chatbots find the answers to questions, and as employees interact with the chatbot, it grows more intelligent based on the feedback from them.

The document management piece enables HR to write or import HR policies and the case management system comes into play when the situation is too complex for the chatbot to handle and it has to be escalated to a human HR representative.

When we spoke to Jain in September 2018 at the time of his startup’s $2 million seed round, he had 16 customers and hoped to have 50 in the next 12-18 months. Today the company has 100 enterprise customers with 300,000 employees using the platform worldwide.

In fact, the pandemic has fueled business with more than half of those customers coming on board this year. He says this is because companies are looking for ways to digitize processes like HR as employees are working from home more.

“This is a trend that’s going to continue as organizations have realized the value of doing things with more and more digital applications taking care of your processes […] especially mundane, repeatable tasks being handed over to technology more and more,” Jain said.

As the business has grown this year, the company has expanded from 30 to 75 employees and he hopes to double that number in the next year. As he does, he has discussed with his lead investor how to build a diverse and inclusive culture at Leena AI .

One thing he is trying to do is raise some money from a diverse group of investors, approximately $400,000, and his hope is that these diverse investors can help him build solid diversity programs as he adds employees to his growing company.

That the startup hasn’t only grown during these turbulent times, but thrived, shows that companies are looking to modernize every part of the enterprise technology stack, and that includes HR.

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Warren gets $1.4 million to help local cloud infrastructure providers compete against Amazon and other giants

Started as a side project by its founders, Warren is now helping regional cloud infrastructure service providers compete against Amazon, Microsoft, IBM, Google and other tech giants. Based in Tallinn, Estonia, Warren’s self-service distributed cloud platform is gaining traction in Southeast Asia, one of the world’s fastest-growing cloud service markets, and Europe. It recently closed a $1.4 million seed round led by Passion Capital, with plans to expand in South America, where it recently launched in Brazil.

Warren’s seed funding also included participation from Lemonade Stand and angel investors like former Nokia vice president Paul Melin and Marek Kiisa, co-founder of funds Superangel and NordicNinja.

The leading global cloud providers are aggressively expanding their international businesses by growing their marketing teams and data centers around the world (for example, over the past few months, Microsoft has launched a new data center region in Austria, expanded in Brazil and announced it will build a new region in Taiwan as it competes against Amazon Web Services).

But demand for customized service and control over data still prompt many companies, especially smaller ones, to pick local cloud infrastructure providers instead, Warren co-founder and chief executive officer Tarmo Tael told TechCrunch.

“Local providers pay more attention to personal sales and support, in local language, to all clients in general, and more importantly, take the time to focus on SME clients to provide flexibility and address their custom needs,” he said. “Whereas global providers give a personal touch maybe only to a few big clients in the enterprise sectors.” Many local providers also offer lower prices and give a large amount of bandwidth for free, attracting SMEs.

He added that “the data sovereignty aspect that plays an important role in choosing their cloud platform for many of the clients.”

In 2015, Tael and co-founder Henry Vaaderpass began working on the project that eventually became Warren while running a development agency for e-commerce sites. From the beginning, the two wanted to develop a product of their own and tested several ideas out, but weren’t really excited by any of them, he said. At the same time, the agency’s e-commerce clients were running into challenges as their businesses grew.

Tael and Vaaderpass’s clients tended to pick local cloud infrastructure providers because of lower costs and more personalized support. But setting up new e-commerce projects with scalable infrastructure was costly because many local cloud infrastructure providers use different platforms.

“So we started looking for tools to use for managing our e-commerce projects better and more efficiently,” Tael said. “As we didn’t find what we were looking for, we saw this as an opportunity to build our own.”

After creating their first prototype, Tael and Vaaderpass realized that it could be used by other development teams, and decided to seek angel funding from investors, like Kiisa, who have experience working with cloud data centers or infrastructure providers.

Southeast Asia, one of the world’s fastest-growing cloud markets, is an important part of Warren’s business. Warren will continue to expand in Southeast Asia, while focusing on other developing regions with large domestic markets, like South America (starting with Brazil). Tael said the startup is also in discussion with potential partners in other markets, including Russia, Turkey and China.

Warren’s current clients include Estonian cloud provider Pilw.io and Indonesian cloud provider IdCloudHost. Tael said working with Warren means its customers spend less time dealing with technical issues related to infrastructure software, so their teams, including developers, can instead focus on supporting clients and managing other services they sell.

The company’s goal is to give local cloud infrastructure providers the ability to meet increasing demand, and eventually expand internationally, with tools to handle more installations and end users. These include features like automated maintenance and DevOps processes that streamline feature testing and handling different platforms.

Ultimately, Warren wants to connect providers in a network that end users can access through a single API and user interface. It also envisions the network as a community where Warren’s clients can share resources and, eventually, have a marketplace for their apps and services.

In terms of competition, Tael said local cloud infrastructure providers often turn to OpenStack, Virtuozzo, Stratoscale or Mirantis. The advantage these companies currently have over Warren is a wider network, but Warren is busy building out its own. The company will be able to connect several locations to one provider by the first quarter of 2021. After that, Tael said, it will “gradually connect providers to each other, upgrading our user management and billing services to handle all that complexity.”

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WeWork employees used an alarmingly insecure printer password

A shared user account used by WeWork employees to access printer settings and print jobs had an incredibly simple password — so simple that a customer guessed it.

Jake Elsley, who works at a WeWork in London, said he found the user account after a WeWork employee at his location mistakenly left the account logged in.

WeWork customers like Elsley normally have an assigned seven-digit username and a four-digit passcode used for printing documents at WeWork locations. But the username for the account used by WeWork employees was just four-digits: “9999”. Elsley told TechCrunch that he guessed the password because it was the same as the username. (“9999” is ranked as one of the most common passwords in use today, making it highly insecure.)

The “9999” account is used by and shared among WeWork community managers, who oversee day-to-day operations at each location, to print documents for visitors who don’t have accounts to print on their own. The account cannot be used to access print jobs sent to other customer accounts.

Elsley said that the “9999” account could not see the contents of documents beyond file names, but that logging in to the WeWork printing web portal could allow him to release other people’s pending print jobs sent to the “9999” account to any other WeWork printer on the network.

The printing web portal can only be accessed on WeWork’s Wi-Fi networks, said Elsley, but that includes the free guest Wi-Fi network which doesn’t have a password, and WeWork’s main Wi-Fi network, which still uses a password that has been widely circulated on the internet.

Elsley reached out to TechCrunch to ask us to alert the company to the insecure password.

“WeWork is committed to protecting the privacy and security of our members and employees,” said WeWork spokesperson Colin Hart. “We immediately initiated an investigation into this potential issue and took steps to address any concerns. We are also nearing the end of a multi-month process of upgrading all of our printing capabilities to a best in class security and experience solution. We expect this process to be completed in the coming weeks.”

WeWork confirmed that it had since changed the password on the “9999” user account.

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Is fintech’s Series A market hot, or just overhyped?

Ryan Falvey
Contributor

Ryan Falvey is co-founder and managing partner at Financial Venture Studio, an early-stage fintech venture capital firm.
More posts by this contributor

Theo Katsoulis
Contributor

According to industry reports, venture capital deal-making has notably rebounded since dropping off briefly in March as shelter-in-place orders gripped much of the country.

As seed-stage fintech investors, this has certainly been our experience: “Hot” deals are getting funded faster than ever, and we increasingly see the large multistage global funds competing for the earliest access to companies. However, in our experience and anecdotal conversations with other early-stage investors, that excitement has not been translating to the Series A stage.

We’ve increasingly wondered if the Series A market in fintech is really as hot as it seems. As pre-seed and seed-stage investors, we know that the health of the Series A market is of critical importance.

In early October 2020, the Financial Venture Studio put together a brief survey of the Series A market in fintech and shared it with more than 100 investors with whom we work closely. Despite the high-level numbers indicating a healthy market, our research indicates a market that remains in flux, with significant ramifications for early-stage founders.

Why Series A is so interesting

Although the seed and pre-seed fintech market continues to attract substantial entrepreneurial and investor interest, it is also in some ways one of the easiest parts of the market to fund. The check size is smaller, the velocity of new deals is highest, and while the potential returns are also the highest, this is also the part of the market where information is most scarce. Perhaps counterintuitively, the fact that there is so little information on a business — aside from a plan, a team and maybe some early anecdotal evidence to support the vision — actually makes it easier to “pull the trigger” on deals where those data points align. There just often isn’t a lot more to dig into.

Similarly, by the time a company is raising Series B capital, they typically have some objective evidence that the idea is working. Companies are typically generating revenue, small teams have grown and become more sophisticated in how they operate, and importantly, the governance functions of a company have (hopefully) begun to take shape. The simple existence of a board member with invested capital at stake means that some of the more existential risks of the earliest stage have been mitigated.

In contrast, one of the big milestones for any startup has been to raise a Series A from an institutional investor. Besides an infusion of capital (which is often 2-3x the aggregate capital a company may have raised since its inception), this “stamp of approval” lends credibility to a small company that is trying to hire talent, sell to customers, and, in most cases, raise substantial subsequent capital.

Thus, it’s critical that Series A investors remain active; if not, many of these upstart companies may fail due to a lack of investment, even if they are able to demonstrate early market traction. The Series A funding market is one of — if not the most — critical funding stage in the innovation economy because it acts as a bridge between scrappy early innovation and commercialization at scale.

It stands to reason, then, that dollar amounts invested may not be the best barometer of the ecosystem’s health. What really matters is the volume of companies being funded and the variety of product approaches being pursued.

The post-COVID Series A

Once the initial shock of the pandemic wore off, the VC community had to get back to business, which admittedly is harder to do for funds that write $10 million+ checks and like getting to know founders in person. Still, Series A investors made it a point to let entrepreneurs know they were, and continue to be, “open for business.”

As investors have gotten more comfortable with the new normal, they have been more open to a virtual diligence process. Of the firms we surveyed, only 15% stated they have not completed a Series A investment during COVID-19 work restrictions. Of the firms who completed a Series A investment during COVID-19 (~85%), about half invested in a company whose founder(s) they had a limited or no relationship with prior to the onset of shelter-in-place orders.

The shift to a virtual environment means that process is more important than ever. Numerous investors have cited their renewed focus on following a structured approach to sourcing and diligence. The interpersonal aspect remains important to close a deal, but customer references, referrals from trusted seed-stage investors and a heightened scrutiny of metrics are all at the forefront of investors’ evaluations.

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Is Wall Street losing its tech enthusiasm?

This is The TechCrunch Exchange, a newsletter that goes out on Saturdays, based on the column of the same name. You can sign up for the email here.

Over the past few months the IPO market made it plain that some public investors were willing to pay more for growth-focused technology shares than private investors. We saw this in both strong tech IPO pricing — the value set on companies as they debut — and in resulting first-day valuations, which were often higher.

One way to consider how far public valuations rose for tech startups, especially those with a software core in 2020, is to ask yourself how often you heard about a down IPO this year. Maybe a single time? At most? (You can catch up on 2020 IPO performance here, if you need to.)

IPO enthusiasm exposed a gap between what many venture capitalists and private investors were paying for tech shares, and what the public market was doing with its own valuation calculations. Insurtech startup Hippo’s $150 million private round from July is a good example. The company was valued at $1.5 billion in the round, a healthy uptick from its preceding private valuation. But if we valued it like the then-newly-public Lemonade, a related company, at the time, Hippo was priced inexpensively.

This week, however, the concept of private investors being more conservative than public investors in certain cases (some eight-figure private rounds happened this year at valuations that were even more bullish than public investor treatment of IPOs, to be clear) took a ding as most big tech companies lost ground, SaaS stocks sold off, and other tech firms struggled to keep up with investor enthusiasm.

Not only tech companies took a beating, but as I write to you on this Friday afternoon, the American stock markets were on a path for their worst week since March, CNBC reported, “led by major tech shares.”

A change in the wind? Perhaps. 

Notable is that it was just in September that VCs seemed resigned to having startup valuations pulled higher by public markets’ endless optimism for related companies. Canaan’s Maha Ibrahim told me during Disrupt 2020 that it was a time when VCs had to “play the game” and pay up for startups, so long as companies were being “rewarded in the public markets for high growth the way that Snowflake” was at the time. A16z’s David Ulevitch concurred.

Perhaps that dynamic is changing as stocks dip. If so, startup valuations could decline en masse, along with the more exotic areas of startup-related finance. The SPAC boom, for example, may wane. Chatting with Hippo’s CEO Assaf Wand this week, he posited that SPACs were a market-response to the public-private valuation gap, an accelerant-cum-bridge to help startups get public while demand was hot for their equity.

Without the same red-hot demand for growth and risk, SPACs could cool. So, too, could private valuations that the hottest startups have taken for granted. Whether what we’re feeling in the wind this week is a hiccup or tipping point is not clear. But the public market’s fever for tech equities may have broken at a somewhat awkward time for Airbnb, Coinbase, DoorDash and other not-quite-yet-IPOs.

Market Notes

It started to snow this week where I live, putting a somewhat sad cap on an otherwise turbulent week. Still! There’s lots from our world to get into. Here’s our week’s market notes:

  • Remember when we dug into how quickly startups grew in Q3? Another company that I’ve covered before, Drift, wrote in. The Boston-based marketing software company reported to The Exchange that it grew more than 50% in Q3 compared to the year-ago quarter, with its CEO adding that June and Q3 were the strongest month and three-month periods in its history.
  • The fintech boom continued with DriveWealth raising nearly $57 million this week, with the startup being yet another API-driven play. That a company sitting in-between two key startup trends of the year is doing well is not surprising. DriveWealth helps other fintech companies provide users access to the American equities markets. Alpaca, which also recently raised, is working along similar lines.

This week featured two IPOs that we cared about. MediaAlpha’s debut, giving the advertising-and-insurtech company a $19 per-share IPO price, quickly exploded out of the gate. Today the company is worth nearly $38 per share. Why? On its IPO day MediaAlpha CEO Steve Yi said that he had chosen the current moment because public markets had garnered an appreciation for insurtech. His share price growth seems to concur.

Until we look at Root, to some degree. Root, a neo-insurance provider focused on the automotive space, priced at $27 when it debuted this week, $2 above the top-end of its range. The company is now worth less than $24 per share. So, whatever wave MediaAlpha caught appears to have missed Root. 

I honestly don’t know what to make of the difference in the two debuts, but please email in if you do know (you can just reply to this email, and I’ll get your note).

Regardless, I chatted with Root CEO Alex Timm after his company went public. The executive said that Root had laid down plans to go public a year ago, and that it can’t control market noise around the time of its debut. Timm stressed the amount of capital that Root added to its coffers — north of $1 billion — is a win. I asked how the company intended to not fuck up its newly swollen accounts, to which Timm said that his company was going to stay “laser focused” on its core automotive insurance opportunity.

Oh, and Root is based in Ohio. I asked what its debut might mean for Midwest startups. Timm was positive, saying that the IPO could highlight that there are a lot of smart folks and GDP in the middle of the country, even if venture capital tallies for the region remain underdeveloped.

  • I know that by now you are tired of earnings, but Five9 did something that other companies struggled to accomplish, namely, beat expectations and bolstered its forward guidance. Its shares soared. The Exchange got on the phone with the call center software company to chat about its latest acquisition and earnings. How did it crush expectations as it did? By selling a product that its market needed when COVID-19 hit, the accelerating digital transformation more broadly, and rising e-commerce spend, which is driving more customer support work onto phone lines, it said. A lot of stuff at once, in other words. 
  • Five9 took on a bunch of convertible debt earlier this year, despite making gobs of adjusted profit. I asked its CEO Rowan Trollope how he was going to go about investing cash to take advantage of market tailwinds, while not overspending. He said that the company takes very regular looks at revenue performance, helping it tailor new spend nimbly. It’s apparently working.
  • What else? Peek this week at big, important rounds from SimilarWeb, PrimaryBid and EightFold, a company that I have known for some time. Oh, and I covered The Wanderlust Group’s Series B and Teampay’s Series A extension, which were good fun.

Various and Sundry

  • What’s going on in the world of venture debt as VC gets back to form? We dug in.
  • For the Europhiles amongst us, here’s what’s up with the continent’s VC receipts.
  • Here are 10 favorites from recent Techstars demo days.
  • And here’s some mathmagic about Databricks, after it was rumored to have an H1 2021 IPO target.
  • We’re way out of space this week, but I have some fun stuff in the tank for later, including a Capital G investor’s take on RPA, a call with the CEO of Zapier about no-code/low-code growth and notes from a chat about developer ecosystems with Dell Capital. More on all of that when the news calms down.

Stay safe, and vote.

Alex

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MG Siegler talks portfolio management and fundraising 6 months into the COVID-19 pandemic

This week, GV General Partner (and TechCrunch alum) MG Siegler joined us on Extra Crunch Live for a far-ranging chat about what it takes to foster a good relationship between investor and startup, how portfolio management and investing has changed as the COVID-19 crisis drags on, and what Siegler expects will and won’t stick around in terms of changes in behavior in investment and entrepreneurship once the pandemic passes.

We last caught up with Siegler on the heels of his investment in Universe, a mobile-focused, e-commerce business-building startup. The coronavirus pandemic was relatively new and no one was sure how long it would last or what measures to contain it would look like. Now, with a few months of experience under his belt, Siegler told me that things have relatively settled into a new normal from his perspective as an investor – sometimes for worse, sometimes for better, but mostly just resulting in differences that require adaptation.

This select transcript has been edited for length and clarity. Aside from section headers, all text below is taken from MG Siegler’s responses to my questions.

Business impacts of coping with the pandemic six months on

Just talking about the business side of the equation, I do think that things have sort of stabilized in the day-to-day world here. For us, certainly, I think it’s it’s just as much of a factor though, of just learning how to operate in this in this weird and surreal environment, and knowing how to do remote meetings better. Knowing how to hop on quick Zoom calls, Hangouts, and phone calls, with portfolio companies, to help put out fires, and doing all board meetings remotely, and all that sort of stuff.

That seems like it’s pretty straightforward on paper, but in day-to-day operations, these are all different little learning things that you have to do and come across. I do feel like things are operating in a pretty streamlined manner, or as much as they can be at this point. But, you know, there’s always going to be some more wildcards – like we’re a week away, today, from from the US election.

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