The rest of the world may be slowing down as we prepare for Christmas and the new year, but we are not taking our foot off the gas.

Alex Wilhelm keeps a close watch on the public markets in his column The Exchange, but this week, he branched out to look at some of the metrics underpinning soaring cryptocurrency prices and turned his gaze on StockX, the consumer reseller marketplace that just raised $275 million in a Series E that values the company at approximately $2.8 billion.

“Selling a tenth of your company for north of a quarter-billion may be somewhat common among late-stage software startups with tremendous growth,” he says, but “don’t laugh — the round actually makes pretty OK sense.”

Our staff continues to file their end-of-year stories: We ran a post this morning by Manish Singh that studies India’s massive total addressable market for retail. The nation has more than 60 million mom-and-pop neighborhood stores, and companies like Walmart and Amazon are eager to offer help with payments, logistics and inventory management — as are hundreds of native and foreign startups.

In an interview with author and MIT professor Sinan Aral, Managing Editor Danny Crichton discussed some of the debates currently swirling around the desire in some quarters to regulate social media platforms. In “The Hype Machine,” Aral explores topics like neuroscience, economics and misinformation before offering potential solutions for resolving what he calls “a full-blown social media crisis.”

The stories that follow are an overview of Extra Crunch from the last five days. Complete articles are only available to members, but you can use discount code ECFriday to save 20% off a one or two-year subscription. Details here.

Thank you very much for reading Extra Crunch this week; I hope you have a safe, relaxing weekend!

Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist

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Unpacking Poshmark’s IPO filing

How did fashion marketplace Poshmark go from posting regular losses in 2019 to generating net income in 2020?

After the company filed a public S-1 last night, Alex Wilhelm pondered the question this morning in The Exchange.

Like many e-commerce platforms, Poshmark saw a surge in activity during the COVID-19 pandemic, but it also slashed its marketing spend, which helped boost profits. As the cash-rich company prepares its road show, “Poshmark is valuable,” Alex concluded.

“How valuable the market will decide. But who will it enrich with its final pricing decision?”

Just how bad is that hack that hit US government agencies?

The breach of FireEye and SolarWinds by hackers working on behalf of Russian intelligence is “the nightmare scenario that has worried cybersecurity experts for years,” reports Zack Whittaker.

The intrusion began several months ago, but news of the breach wasn’t made public until this week.

“Given that potential victims include defense contractors, telecoms, banks, and tech companies, the implications for critical infrastructure and national security, although untold at this point, could be significant,” said Erin Kenneally, director of cyber risk analytics at Guidewire, an industry platform for insurance carriers.

In his analysis for Extra Crunch, Zack breaks down the rippling effects of supply-chain attacks that can compromise platforms like SolarWinds, which is used by more than 420 of the Fortune 500.

From startups to Starbucks: The embedded API opportunity

Embedded finance connects services like payment processing with everyday activities like grabbing a coffee before unlocking an e-scooter.

“The ability to be at the right place at the right time, supporting consumers and merchants alike, where they want it, how they want it and when they want it — cannot be understated,” says Simon Wu, an investment director with Cathay Innovation.

In a post that identifies embedded finance’s top providers and enablers, he offers advice for startups and established brands that are hoping to “earn and build customer loyalty while generating new revenue streams.”

Is rising usage driving crypto’s recent price boom?

Bitcoin is at an all-time high.

CoinMarketCap reports that crypto market values have reached almost $659 billion; that figure was just $140 billion in March 2020.

“These gains have created a huge amount of wealth for crypto holders,” Alex Wilhelm wrote yesterday.

To get a better handle on why crypto values are sky-bound, he parsed some basic industry metrics, including the number of unique bitcoin addresses, fees paid and transactions per day.

“Do the price gains make sense in the short term? Who knows,” he wrote, “but they are not based on nothing.”

2020 was a disaster, but the pandemic put security in the spotlight

For his year-end Extra Crunch story, security reporter Zack Whittaker looked back at the myriad security challenges and vulnerabilities COVID-19 brought to the fore.

The hacks of Fire Eyes and SolarWinds were just one link in the chain: How well is your company prepared to deal with file-encrypting malware, hackers backed by nation-states or employees accessing secure systems from home?

“With 2020 wrapping up, much of the security headaches exposed by the pandemic will linger into the new year,” says Zack.

Inside Zoox’s six-year ride from prototype to product

After six years of research and development, autonomous vehicle company Zoox this week unveiled an electric robotaxi that can carry four people at a maximum speed of 75 miles per hour.

Automotive writer Kirsten Korosec interviewed Zoox co-founder and CTO Jesse Levinson to learn more about the vehicle’s development and how the company overcame a series of technical and legal challenges.

“I would say that if you have a big idea and you’re confident that it makes sense, you should at least explore the idea, rather than giving up because the current regulations aren’t designed for it,” said Levinson.

Kirsten only had 15 minutes to interview Levinson, but this comprehensive interview covers topics like regulatory compliance, Zoox’s relationship with parent company Amazon and the highest (and lowest) moments he experienced along the way.

Pluralsight $3.5B deal signals a matured edtech market

In one of the largest enterprise acquisitions of 2020, Visa Equity Partners this week purchased Utah-based edtech startup Pluralsight for $3.5 billion.

According to the entrepreneurs and investors reporter Natasha Mascarenhas spoke to, this deal “shows the strength of edtech’s capital options as the pandemic continues.”

“What’s happening in edtech is that capital markets are liquidating,” a major change from “the old days where the options to exit were very narrow,” says Deborah Quazzo, a managing partner at GSV Advisors and seed investor in Pluralsight.

Dear Sophie: How did immigration change for startup founders in 2020?

Dear Sophie:

I’m on an F1 OPT and am about to incorporate a startup with my two American co-founders.

What were the biggest immigration changes in 2020 affecting us?

—Ambitious in Albany

How to pick an investor in good or bad times

Founders and the VCs who back them may not be friends, but they’re usually friendly.

Investors are on a first-name basis with entrepreneurs from their portfolio companies and frequently have candid conversations with them about life, work and the world in general. In the before times, they might even have shared a meal or attended a baseball game together.

But make no mistake, it is a top-down relationship — the investor will always have the upper hand. When an entrepreneur accepts a check, they are hiring their next boss.

In an Extra Crunch guest post, Quiq CEO and founder Mike Myer poses two questions for founders who are considering a new relationship with a VC:

• How can the investor help the business?
• What’s the risk that the investor will hurt the business?

From India’s richest man to Amazon and 100s of startups: The great rush to win neighborhood stores

In India, about 90% of consumers buy their everyday goods from neighborhood-based kirana stores instead of supermarkets.

As a result, U.S. retail giants like Walmart and Amazon have adopted an “if you can’t beat them, join them” approach, offering the nation’s 60 million mom-and-pop shops software for inventory control, payments and e-commerce.

India’s retail market will be worth an estimated $1.3 trillion by 2025, but e-commerce represents just 3% of that activity today, reports Manish Singh.

For his final Extra Crunch story of 2020, he looked at the startups and major players who are hoping to carve out their niche in one of the world’s largest retail ecosystems.

ClickUp CEO talks hiring, raising and scaling in the white-hot productivity space

Earlier this year, business productivity software startup ClickUp raised a $35 million Series A.

Now, just six months later, the company has closed a second round of $100 million that values the San Diego-based startup at $1 billion.

Lucas Matney interviewed CEO Zeb Evans this week to learn more about how the company was buoyed by pandemic-based behavior shifts that doubled its customer base and multiplied revenue by a factor of nine.

“I think that the biggest thing that we’ve always focused on is shipping a new version of ClickUp every week. That is our differentiation,” he said. “We’ve kind of created these iterative cycles called natural product-market fit and it’s been hard to keep up with that.”

2020’s top 10 enterprise M&A deals totaled a staggering $165B

In 2018, the total value of the year’s 10 top enterprise mergers and acquisitions reached $87 billion; last year, that figure fell to just $40 billion.

But in 2020, 10 M&A deals accounted for $165.2 billion.

“Last year’s biggest deal — Salesforce buying Tableau for $15.7 billion — would have only been good for fifth place on this year’s list,” notes enterprise reporter Ron Miller. “And last year’s fourth largest deal, where VMware bought Pivotal for $2.7 billion, wouldn’t have even made this year’s list at all.”

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We’ve seen a big wave of proptech startups emerge to reimagine how houses and bought and sold, with some tapping into the opportunity with distressed property, and others exploring the “iBuyer” model where houses are bought, fixed up and resold by a single startup to homeowners who don’t want to invest in a fixer-upper. But the vast majority of homes are still sold the traditional way, by way of a real estate agent working via a broker.

Today, a startup is announcing that it has raised seed funding not to disrupt, but improve that basic model with a more flexible approach that can help agents work in a more modern way, and to ultimately scale out the number of people working as agents in the market.

Avenue 8, which describes itself as a “mobile-first residential real estate brokerage” — providing a new set of tools for agents to source, list and sell homes, and handle the other aspects of the process that fall between those — has raised $4 million. This is a seed round, and Avenue 8 plans to use it to expand further in the cities where it is already active — it’s been in beta thus far in the San Francisco and Los Angeles areas — as well as grow to several more.

The funding is notable because of the backers that the startup has attracted early on. It’s being led by Craft Ventures — the firm co-founded by David Sacks and Bill Lee that has amassed a prolific and impressive portfolio of companies — with Zigg Capital, and Good Friends (an early-stage fund from the founders of Warby Parker, Harry’s, and Allbirds) also participating.

There has been at least $18 billion in funding raised by proptech companies in the last decade, and with that no shortage of efforts to take the lessons of tech — from cloud computing and mobile technology, through to artificial intelligence, data science, and innovations in e-commerce — and apply them to the real estate market.

Michael Martin, who co-founded Avenue 8 with Justin Fichelson, believes that this pace of change, in fact, means that one has to continually consider new approaches.

“It’s important to remember that Compass’s growth strategy was to roll out its technology to traditional brokerages,” he said of one of the big juggernauts in the space (which itself has seen its own challenges). “But if you built it today, it would be fundamentally different.”

And he believes that “different” would look not unlike Avenue 8.

The startup is based around a subscription model for a start, rather than a classic 30/70 split on the sales commissions that respectively (and typically) exist between brokers and agents.

Around that basic model, Avenue 8 has built a set of tools that provides agents with an intuitive way to use newer kinds of marketing and analytics tools both to get the word out about their properties across multiple channels; analytics to measure how their efforts are doing, in order to improve future listings; and access to wider market data to help them make more informed decisions on valuations and sales. It also providers a marketplace of people — valets — who can help stage and photograph properties for listing, and Avenue 8 doesn’t require payments to be made to those partners unless a home sells.

It also provides all of this via a mobile platform — key for people in a profession that often has them on the move. 

Targeting agents that have in the past relied essentially on using whatever tools the brokers use — which often were simply their own sites plus some aggregating portals — Avenue 8’s pitch is not just better returns but a better process to get there.

“We’ve heard time and time again that agents struggle to identify and leverage the technology and tools to successfully manage their relationships and properties. Changing buyer/seller expectations have accelerated the digital transformation of most agents’ workflows,” said Ryan Orley, Partner at Zigg Capital, in a statement. “Avenue 8 is building and integrating the right software and resources for our new reality.”

What’s also interesting about Avenue 8 is how it can open the door to a wider pool of agents in the longer run.

The real estate market has been noticeably resilient throughout the pandemic, with lower interest rates, a generally lower overall home inventory, and people spending more time at home (and wanting a better space) creating a high level of demand. With a number of other industries feeling the pinch, a flexible platform like Avenue 8’s creates a way for people — who have taken and passed the certifications needed to become agents — to register and flexibly work as an agent as much or as little as they choose, creating a kind of “Uber for real estate agents,” as it were.

That scaling opportunity is likely one of the reasons why this has potentially caught the eye of investors.

“Avenue 8’s organic growth is clear evidence that the market demands a mobile-first, digital platform,” said Jeff Fluhr, General Partner at Craft Ventures, in a statement. “Michael and Justin have a clear vision for modernizing real estate while keeping agents at the center. Avenue 8’s model helps agents take home more even in today’s environment where commissions are compressing.”

Interestingly, just as Uber’s changed the way that on-demand transportation is ordered and delivered, Avenue 8 is starting to see some interesting traction in terms of its place in the real estate market. Although it was originally targeted at agents with the pitch of being like “a better broker” — providing the services brokers are regulated to provide, but with a more modern wrapper around it — it’s also in some cases attracting brokerages, too. Martin said that it’s already working with a few smaller ones, and ultimately might consider ways of providing its tools to larger ones to manage their businesses better.

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