At the end of 2020, I argued that edtech needs to think bigger in order to stay relevant after the pandemic. I urged founders to think less about how to bundle and unbundle lecture experience, and more about how to replace outdated systems and methods with new, tech-powered solutions. In other words, don’t simply put engaging content on a screen, but innovate on what that screen looks like, tracks and offers.

A few months into 2021, the exit environment in edtech…feels like it’s doing exactly that. The same startups that hit billion and multi-billion valuations during the pandemic are scooping up new talent to broaden their service offerings.

Ruben Harris, the founder of Career Karma, a platform that matches aspiring coding professionals to bootcamps, put together a massive report recently with his team to talk about the pandemic’s impact on the bootcamp market.

James Gallagher, the author of the report, tells me:

It is important to note that the full potential of bootcamps has not yet been realised. We are now seeing more exploration of niches like technology sales which provide gateways into new careers in tech for people who otherwise may not have been able to acquire training. To scale such models, new businesses will need venture capital.

He went on to explain how a notable acquisition from 2020 was K12 scooping up Galvanize, “which would give K12 exposure into corporate training and the coding bootcamp space, a market outside of K12’s focus at the moment.”

To me this report signal two things: the financial interest in boot camps isn’t simply stemming from other bootcamps (although that is happening), but it’s surprising partnerships. Leaving this subsector, we see creative acquisitions such as a Roblox for edtech buying a language learning tool, and a startup known for flashcards scooping up a tech tutoring service.

How is edtech spending its extra capitalByju’s in talks to acquire US-based reading platform, Epic The tech-powered wave of smart, not slow, tutoring sessions

Readers should know by this point that I love a nonobvious acquisition (except when this almost happened), so if you have any more tips on coming deals in edtech, please Signal me or direct message me on Twitter.

I’ll end with this: Successful startup founders are innately ambitious, finding opportunity in moonshots and convincing others that the odds are in their favor. However, the ceiling for what defines ambition heightens almost everyday. What used to be a win is now a nonnegotiable, and a feat is only a feat until your competitor hits the exact same milestone.

Acquisitions are one way to scoop up competition and synergistic talent, but it’s what happens next that matters the most.

In the rest of this newsletter, we will talk about Clubhouse competitors, how a homegrown experiment became one of the fastest growing companies in fitness tech and a cool-down in public markets (?!). As always, you can get this newsletter in your inbox each Saturday morning, so subscribe here to join the cool kids.

Clubhouse might create billions in value, but could capture none of it

Remember when everyone was buzzing around about building Stories? That’s so pre-pandemic. A number of companies recently announced plans to build their own versions of Clubhouse, after the buzzy app unearthed the consumer love for audio.

Here’s what to know: It might be easier to start guessing who isn’t building a Clubhouse clone at this point. Our predictions are already starting, but jokes aside, the rise in clones could mean that Clubhouse might have to make a run for its pre-monetized money (cough, cough, Twitter spaces). It doesn’t matter if a startup is first in unlocking a key insight, all that matters is who executes that key insight the best.

Facebook’s Clubhouse rival looks a lot like Clubhouse right nowDiscord is launching new Clubhouse-like channels for audio events LinkedIn confirms it’s working on a Clubhouse rival, tooSwell launches its app for asynchronous voice conversations Slack wants to be more than a text-based messaging platform Twitter Spaces arrives on Android ahead of ClubhouseSpotify is getting into live audio because of course it isCareer Karma built audio roomsChina’s Clubhouse clones via Protocol

A strong unicorn, literally

Tonal, a fitness tech startup, became a unicorn this week after raising a new tranche of capital.

Here’s what to know: The new status underscores market growth for at-home fitness solutions. And while we don’t have a Tonal S-1 yet, we do have a Tonal EC-1. EC-1’s are TechCrunch’s riff on an S-1, and are essentially a deep dive into a company.

Reporter JP Mangalindan wrote thousands and thousands of words about Tonal, from its origin story to business model, its focus on communities and its biggest hurdles ahead.

How a homegrown experiment became one of the fastest-growing companies in fitness techMillions of dollars and 3.5 years, and it all came down to thisBuilding online communities for fun, profit and productCan Tonal become the luxury fitness market champion?

Initial public o….no

You’ve probably had a better week than Compass, Deliveroo and Kaltura. The three companies all had different events that illustrate a potential damper on the part that has been the public markets.

Here’s what to know: Compass cut its shares and lowered pricing of said shares, Deliveroo had a rough debut as a delivery company on the public markets, and Kaltura postponed its IPO after valuation demand didn’t hit expectations.

In other news, though:

Coursera prices IPO at top end of its range in boon to edtech valuations Coinbase to direct list on April 14th, provide financial update on April 6thUiPath’s IPO filing suggests robotic process automation is booming

Around TechCrunch

Thanks to everyone who tuned in to TechCrunch Early Stage! If you enjoyed the event (or missed it), don’t worry: Disrupt is almost here.

Buy a pass to Disrupt 2021 and get a free Extra Crunch membershipAnd I want to give a shout-out to two newsletters that I hope you read each week along with Startups Weekly: This Week in Apps and The Exchange. 

Across the week

Seen on TechCrunch

How startups can go passwordless, thanks to zero trust

Tips for founders thinking about doing a remote accelerator

US iPhone users spent an average of $138 on apps in 2020, will grow to $180 in 2021

Niantic CEO shares teaser image of AR glasses device

The Weeknd will sell an unreleased song and visual art via NFT auction

Seen on Extra Crunch

Embedded procurement will make every company its own marketplace

5 mistakes creators make building new games on Roblox

E-commerce roll-ups are the next wave of disruption in consumer packaged goods

How our SaaS startup improved net revenue retention by more than 30 points in two quarters

For this morning’s column, Alex Wilhelm looked back on the last few months, “a busy season for technology exits” that followed a hot Q4 2020.

We’re seeing signs of an IPO market that may be cooling, but even so, “there are sufficient SPACs to take the entire recent Y Combinator class public,” he notes.

Once we factor in private equity firms with pockets full of money, it’s evident that late-stage companies have three solid choices for leveling up.

Seeking more insight into these liquidity options, Alex interviewed:

DigitalOcean CEO Yancey Spruill, whose company went public via IPO.Latch CFO Garth Mitchell, who discussed his startup’s merger with real estate SPAC $TSIA.Brian Cruver, founder and CEO of AlertMedia, which recently sold to a private equity firm.

After recapping their deals, each executive explains how their company determined which flashing red “EXIT” sign to follow. As Alex observed, “choosing which option is best from a buffet’s worth of possibilities is an interesting task.”

Thanks very much for reading Extra Crunch! Have a great weekend.

Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist

Full Extra Crunch articles are only available to members.
Use discount code ECFriday to save 20% off a one- or two-year subscription.

The Tonal EC-1

On Tuesday, we published a four-part series on Tonal, a home fitness startup that has raised $200 million since it launched in 2018. The company’s patented hardware combines digital weights, coaching and AI in a wall-mounted system that sells for $2,995.

By any measure, it is poised for success — sales increased 800% between December 2019 and 2020, and by the end of this year, the company will have 60 retail locations. On Wednesday, Tonal reported a $250 million Series E that valued the company at $1.6 billion.

Our deep dive examines Tonal’s origins, product development timeline, its go-to-market strategy and other aspects that combined to spark investor interest and customer delight.

We call this format the “EC-1,” since these stories are as comprehensive and illuminating as the S-1 forms startups must file with the SEC before going public.

Here’s how the Tonal EC-1 breaks down:

Part 1: How a homegrown experiment became one of the fastest-growing companies in fitness techPart 2: Millions of dollars and 3.5 years, and it all came down to thisPart 3: Building online communities for fun, profit and productPart 4: Can Tonal become the luxury fitness market champion?

We have more EC-1s in the works about other late-stage startups that are doing big things well and making news in the process.

What to make of Deliveroo’s rough IPO debut

Why did Deliveroo struggle when it began to trade? Is it suffering from cultural dissonance between its high-growth model and more conservative European investors?

Let’s peek at the numbers and find out.

Kaltura puts debut on hold. Is the tech IPO window closing?

The Exchange doubts many folks expected the IPO climate to get so chilly without warning. But we could be in for a Q2 pause in the formerly scorching climate for tech debuts.

Is Substack really worth $650M?

A $65 million Series B is remarkable, even by 2021 standards. But the fact that a16z is pouring more capital into the alt-media space is not a surprise.

Substack is a place where publications have bled some well-known talent, shifting the center of gravity in media. Let’s take a look at Substack’s historical growth.

RPA market surges as investors, vendors capitalize on pandemic-driven tech shift

Robotic process automation came to the fore during the pandemic as companies took steps to digitally transform. When employees couldn’t be in the same office together, it became crucial to cobble together more automated workflows that required fewer people in the loop.

RPA has enabled executives to provide a level of automation that essentially buys them time to update systems to more modern approaches while reducing the large number of mundane manual tasks that are part of every industry’s workflow.

E-commerce roll-ups are the next wave of disruption in consumer packaged goods

This year is all about the roll-ups, the aggregation of smaller companies into larger firms, creating a potentially compelling path for equity value. The interest in creating value through e-commerce brands is particularly striking.

Just a year ago, digitally native brands had fallen out of favor with venture capitalists after so many failed to create venture-scale returns. So what’s the roll-up hype about?

Hack takes: A CISO and a hacker detail how they’d respond to the Exchange breach

The cyber world has entered a new era in which attacks are becoming more frequent and happening on a larger scale than ever before. Massive hacks affecting thousands of high-level American companies and agencies have dominated the news recently. Chief among these are the December SolarWinds/FireEye breach and the more recent Microsoft Exchange server breach.

Everyone wants to know: If you’ve been hit with the Exchange breach, what should you do?

5 machine learning essentials nontechnical leaders need to understand

Machine learning has become the foundation of business and growth acceleration because of the incredible pace of change and development in this space.

But for engineering and team leaders without an ML background, this can also feel overwhelming and intimidating.

Here are best practices and must-know components broken down into five practical and easily applicable lessons.

Embedded procurement will make every company its own marketplace

Embedded procurement is the natural evolution of embedded fintech.

In this next wave, businesses will buy things they need through vertical B2B apps, rather than through sales reps, distributors or an individual merchant’s website.

Knowing when your startup should go all-in on business development

There’s a persistent fallacy swirling around that any startup growing pain or scaling problem can be solved with business development.

That’s frankly not true.

Dear Sophie: What should I know about prenups and getting a green card through marriage?

Dear Sophie:

I’m a founder of a startup on an E-2 investor visa and just got engaged! My soon-to-be spouse will sponsor me for a green card.

Are there any minimum salary requirements for her to sponsor me? Is there anything I should keep in mind before starting the green card process?

— Betrothed in Belmont

Startups must curb bureaucracy to ensure agile data governance

Many organizations perceive data management as being akin to data governance, where responsibilities are centered around establishing controls and audit procedures, and things are viewed from a defensive lens.

That defensiveness is admittedly justified, particularly given the potential financial and reputational damages caused by data mismanagement and leakage.

Nonetheless, there’s an element of myopia here, and being excessively cautious can prevent organizations from realizing the benefits of data-driven collaboration, particularly when it comes to software and product development.

Bring CISOs into the C-suite to bake cybersecurity into company culture

Cyber strategy and company strategy are inextricably linked. Consequently, chief information security officers in the C-suite will be just as common and influential as CFOs in maximizing shareholder value.

How is edtech spending its extra capital?

Edtech unicorns have boatloads of cash to spend following the capital boost to the sector in 2020. As a result, edtech M&A activity has continued to swell.

The idea of a well-capitalized startup buying competitors to complement its core business is nothing new, but exits in this sector are notable because the money used to buy startups can be seen as an effect of the pandemic’s impact on remote education.

But in the past week, the consolidation environment made a clear statement: Pandemic-proven startups are scooping up talent — and fast.

Tech in Mexico: A confluence of Latin America, the US and Asia

Knowledge transfer is not the only trend flowing in the U.S.-Asia-LatAm nexus. Competition is afoot as well.

Because of similar market conditions, Asian tech giants are directly expanding into Mexico and other LatAm countries.

 

How we improved net retention by 30+ points in 2 quarters

There’s certainly no shortage of SaaS performance metrics leaders focus on, but NRR (net revenue retention) is without question the most underrated metric out there.

NRR is simply total revenue minus any revenue churn plus any revenue expansion from upgrades, cross-sells or upsells. The greater the NRR, the quicker companies can scale.

5 mistakes creators make building new games on Roblox

Even the most experienced and talented game designers from the mobile F2P business usually fail to understand what features matter to Robloxians.

For those just starting their journey in Roblox game development, these are the most common mistakes gaming professionals make on Roblox.

 

CEO Manish Chandra, investor Navin Chaddha explain why Poshmark’s Series A deck sings

“Lead with love, and the money comes.” It’s one of the cornerstone values at Poshmark. On the latest episode of Extra Crunch Live, Chandra and Chaddha sat down with us and walked us through their original Series A pitch deck.

 

Will the pandemic spur a smart rebirth for cities?

Cities are bustling hubs where people live, work and play. When the pandemic hit, some people fled major metropolitan markets for smaller towns — raising questions about the future validity of cities.

But those who predicted that COVID-19 would destroy major urban communities might want to stop shorting the resilience of these municipalities and start going long on what the post-pandemic future looks like.

 

The NFT craze will be a boon for lawyers

There’s plenty of uncertainty surrounding copyright issues, fraud and adult content, and legal implications are the crux of the NFT trend.

Whether a court would protect the receipt-holder’s ownership over a given file depends on a variety of factors. All of these concerns mean artists may need to lawyer up.

Viewing Cazoo’s proposed SPAC debut through Carvana’s windshield

Woody Sears has long been interested in storytelling. Following the debut in 2007 of the first iPhone, he founded a storytelling app called Zuuka that built up a library of narrated and illustrated kids’ books for the iPhone and iPad.

Sears later sold that company to a small New York-based outfit. But Sears, who is based in Santa Barbara, California, isn’t done with stories yet. Instead, he just raised $1.6 million in seed funding for his second and newest storytelling startup, HearHere, a subscription-based audio road-trip app that, with users’ permission, pushes information to them as they’re driving, giving them informational tidbits in three- to five-minute segments about their surroundings, including points of interest they might not have been aware of at all.

The idea is to surface the unknown or forgotten history of regions, which makes sense in a world where more people have returned to road trips and parents have grown desperate to pull their kids’ attention away from TikTok. In fact, Sears’s neighbor, Kevin Costner, liked the idea so much that he recently joined its five-person team as a co-founder and narrator and investor, along with Snap Inc., the law firm Cooley, Camping World CEO and reality TV star Marcus Lemonis, AAA and numerous other individual investors, including from NextGen Venture Partners.

Because we, too, like history and road trips (and okay, fine, Kevin Costner), we talked with Sears and Costner earlier today to learn why they think they’ll succeed with HearHere when other content-rich geo-location based apps have fallen short of meaningful adoption.

Excerpts from that chat follow, edited lightly for length.

TC: You’re creating an audio map of the U.S., so how many stories do you have banked as we speak?

WS: We’re up to 5,500 stories across 22 states, and we’ll be nationwide by summer. The mission is to connect people to the places that they’re traveling through, lending people stories about the history, the natural wonders and the colorful characters who’ve lived in that area. We also do stories about sports and music and provide local insights.

TC: That’s a lot of content to gather up, edit down, then record. What does the process look like? 

WS: At the end of the day, the content is king, and we take great care with these stories, producing them with a team of 22 researchers, writers, editors and narrators, most whom come from a travel journalism background. We really feel like we get the best end result through that team approach.

Eventually, we’ll open up to third-party content contributors, where we’re hosting both professional content and also user-generated content.

TC: Is there an AI component or will there be?

WS: We more see this as augmented reality in that these stories really do overlay the landscape and give you a different perspective while traveling. But AI and machine learning are things that we’ll incorporate as we start to move into foreign languages and better tailor the content for the end user.

TC: How do you prioritize which stories to tell as you’re building up this content library?

WS: The major historical markers are a big inspiration, but we’re looking for those lesser-known gems, too, and we look at travel patterns — the way that people move when they’re on leisure trips, meaning what interstate highways they’re taking and which scenic routes are most popular.

TC: How does the subscription piece work?

WS: You get five free free stories each month; for unlimited streaming, it’s $35.99 per year.

TC: Kevin, you must be approached a lot with startup ideas and investment opportunities. Why get so involved with this one?

KC: Obviously I’m story-oriented; that doesn’t come as a shock to anybody. But you’re right, a lot of ideas come to me.

HearHere came through my wife, who said that Woody had something he wanted to talk about, and as she explained it to me, I got it, you know? That’s the shiny thing for me, storytelling and having the ability for a good story to come out, especially when it comes to our country.

So we had this meeting and he explained the concept to me, which is kind of equal to what I’d already been doing my whole life, which is stopping at the bronze plaques all over the country and reading about their historical significance — those [moments] that kind of interrupt everybody’s trip except mine. [Laughs.] You know, [it’s] getting out and stretching my legs and reading a little history and dreaming while the rest of the people in the car are kind of moaning because we stopped our progress.

This [product] is an extension of that for me, without getting out of the car, and with stories that can evolve and perhaps get longer. And I can become more involved in what I was driving past and the people in the car can maybe sense what it was that interested me enough to stop.

TC: You love history. 

KC: HearHere is a lot more than history, but for me, it was the history [that I found so compelling]. And it’s how the foundation was set for me to become more involved in the company and understand it a lot better and then become somebody who wanted to be a part of the founding of it.

TC: AAA and Camping World are among the company’s strategic investors. How might they promote the app and what other partnerships have you struck to get HearHere in front of people at the right time?

WS: Camping World also owns Good Sam Club, which is the largest organization of RV owners in the world, and AAA is a giant with 57 million members in the U.S., and they all see this as a way to fulfill something they’re aren’t currently doing for their audience; it’s making that bridge to digital, and we’re really excited to get this in front of their members and customers.

We also have partnerships with [the RV marketplaces] Outdoorsy and RVshare [and the RV rental and sales company] Cruise America. It’s a very hot market.

TC: There have been similar ideas. Caterina Fake’s Findery was an early app that aimed to help users discover much more about locations. Detour, a startup that provided walking audio tours of cities that was founded by Groupon co-founder Andrew Mason, seemed interesting but failed to take off with users. What makes you think this startup will click?

WS: I loved Detour. I ate up both of those.

I guess where I think [Detour] missed product-market fit was the number of scenarios where you could use it and also, it was competing for people’s time. We chose to start with road trips because you have a captive audience; there’s only so much you can do when you’re driving in the car, unlike when you’re in a city, where there are all kinds of options to explore its history, including physical books and tour guides. You also had to carve out two hours of your time, and it’s easy to get distracted while you’re walking around.

We want to capture the places that are along the journey and lesser known and more untold and where people have the space to engage in it. Starting as short form helps. It’s also on-demand, so you don’t have to follow a pre-designated route. We’re not taking you on a specific tour, where you have to turn left or turn right. We’re going to surface stories for you no matter what route you take.

Cross-border payments startup dLocal has raised $150 million at a $5 billion valuation, less than seven months after securing $200 million at a $1.2 billion valuation.

This means that the five-year-old Uruguayan company has effectively quadrupled its valuation in a matter of months.

Alkeon Capital led the latest round, which also included participation from BOND, D1 Capital Partners and Tiger Global. General Atlantic led its previous round, which closed last September and made dLocal Uruguay’s first unicorn and one of Latin American’s highest-valued startups.

DLocal connects global enterprise merchants with “billions” of emerging market consumers in 29 countries across Asia-Pacific, the Middle East, Latin America and Africa. More than 325 global merchants, including e-commerce retailers, SaaS companies, online travel providers and marketplaces use dLocal to accept over 600 local payment methods. They also use its platform to issue payments to their contractors, agents and sellers. Some of dLocal’s customers include Amazon, Booking.com, Dropbox, GoDaddy, MailChimp, Microsoft, Spotify, TripAdvisor, Uber and Zara. 

In conjunction with this latest round, dLocal has named Sumita Pandit to the role of COO. Pandit is former global head of fintech and managing director for JP Morgan, and also worked at Goldman Sachs.

“Sumita is a highly respected and accomplished fintech investment banker, and she’s played a pivotal role advising some of the world’s most successful fintech companies as they’ve scaled to become global leaders,”  said dLocal CEO Sebastián Kanovich in a written statement.

Meanwhile, former COO Jacobo Singer has been promoted to president of dLocal.

The company plans to use its new capital to enhance its technology and continue to expand geographically.

Alkeon General Partner Deepak Ravichandran believes that emerging markets represent some of the fastest growth opportunities in digital payments.

“However, as global merchants look to access these markets, they are often faced with a complex web of local payment methods, cross-border regulations, and other operational roadblocks,” he said in a written statement. “dLocal’s unique platform empowers merchants with a single integrated payment solution, to reach billions of customers, accept payments, send payouts, and settle funds globally.”

The first quarter of 2021 was a busy season for technology exits. Coming off a hot period in the final quarter of 2020, it was no surprise that tech upstarts pursued liquidity through a variety of mechanisms as the new year began.

There were IPOs, there were direct listings, there were PE deals. Hell, we even saw enough SPACs that we lost track of a few; amid all the noise, you’ll miss the occasional note no matter how well-tuned your ear.

The Exchange explores startups, markets and money. Read it every morning on Extra Crunch, or get The Exchange newsletter every Saturday.

Each path is still open for later-stage startups to pursue exits: The IPO market was welcoming until a few minutes ago and private equity firms are stacked with cash and willing to pay higher multiples than they might in more normal times. And there are sufficient SPACs to take the entire recent Y Combinator class public.

Choosing which option is best from a buffet’s worth of possibilities is an interesting task for startup CEOs and their boards.

DigitalOcean went public via a traditional IPO, raising a slug of capital in the process. The SMB-focused public cloud company likely felt like a somewhat obvious IPO candidate when you read its results. The Exchange spoke with the company’s CEO, Yancey Spruill, about the choice.

Latch, in contrast, decided that a SPAC was its best route out the gate. The Exchange caught up with the company’s CFO, Garth Mitchell, about the transaction and why it made sense for his company.

And, finally, The Exchange spoke with AlertMedia’s founder and CEO, Brian Cruver, about his decision to sell his Texas-based company to a private equity firm.

To prevent this post from reaching an astronomic word count, we’ll give a brief overview of each deal and then summarize the company’s views about why their liquidity choice was the right one.

Three paths to liquidity

Kicking off with DigitalOcean, a few notes: First, the company has been pretty darn public about its growth in the last few years. We knew that it had an annualized run rate of around $200 million in 2018, $250 million in 2019 and around $300 million in the first half of 2020. It later announced that it hit that mark in May of last year.

So when DigitalOcean decided to go public, we weren’t bowled over. The company wound up pricing at $47 per share, the high end of its range. Since then, its stock has struggled somewhat, falling below $37 per share before recovering to $43.80 at the end of trading yesterday.

Enough of all that. Why did the company choose to go public via a traditional IPO? Spruill said his company looked at SPAC deals and direct listings. It selected the IPO route because it fit the company’s goals of generating a broad base of shareholders while creating a branding opportunity.

The cost of an IPO is comparable, he added, to other exit options. Spruill also praised the IPO process itself, noting that its rigorous requirements made DigitalOcean a better company.

Earlier in our chat, I asked Spruill a question that I put to every CEO on IPO day: How are you feeling? It’s a bit of a sop, but it sometimes elicits insights from executives and founders who, after weeks of discussing their companies’ inner workings, are asked a rare personal question.

Spruill said he felt incredible and that nothing could replicate an IPO as the culmination of so much work put into building a company and its team. If you add up the wins and losses over time, with more of the former than the latter, and can cross the finish line with the right metrics and market, you can earn a spot to be “grilled” by the “best investors,” he said.

Those investors put $750 million or so into his company, Spruill added. Funds that it can use to retire debt and free up more cash flow. Not a bad day, I’d say.

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast, where we unpack the numbers behind the headlines.

Natasha and Danny and Alex and Grace were all here to chat through the week’s biggest tech happenings. It was a busy week on the IPO front, Danny was buried in getting the Tonal EC-1 out, and Natasha took some time off. But the host trio managed to prep and record a show that was honestly a kick to record, and we think, a pleasure to listen to!

So, for your morning walk, here’s what we have for you:

The Substack conversation: Does the new $65 million check make sense? What is Substack? Does it have a moat? Why is Natasha’s URL so much better than Alex’s?Cameo raised $100 million and none of us really have a bone to pick with that. Danny actually argues in favor of it.The Clubhouse conversation: Does every single product need to feature live audio? The answer appears to be yes, oddly enough. Discord comes up along with Spotify, as does LinkedIn. And somehow, Microsoft Excel and Miami?TechCrunch scooped that Pipe is raising more money at a huge new valuation, and we argue about what a derivative really is.Harlem Capital raises $134 million for its new fund.MaC VC raises $103 million for its new fund.

It was a mix of laughs, ‘aha’ moments and honest conversations about how complex ambition in startups should be. One listener the other day mentioned to us that the pandemic made it harder to carve out time for podcasts, since listening was often reserved for commutes. We get it, and in true scrappy fashion, we’re curious how you’ve adapted to remote work and podcasts. Let us know how you tune into Equity via Twitter and remember that we’re thankful for your ears!

Mike Barile spent two years and racked up nearly $20,000 in credit card debt to bring his first startup, Backflip, to life.

The former management consultant had spent years toiling in the startup grind, first at Uber, then, after taking a coding academy bootcamp through AppAcademy (where Barile met his co-founder, Adam Foosaner), at Google and at a failed cryptocurrency startup.

Burned by the crypto experience, Barile was casting about for his next thing, and trying to find a way to scrape up some rent money, when he hit on the idea for Backflip. The experience of selling electronics online was still shady and Barile and Foosaner thought there had to be a better way.

That way became Backflip. It offers customers cash on delivery for their used electronics — anything from Androids to Xboxes and Apple devices to Game Boys.

“When I first started working on backflip back in March 2019, I met this kid named Chris and he wanted to buy some of my old iPhones. He had been a student at USF and as a side hustle he started buying used devices and would refurbish them and then either sell them himself or sell them to an official reseller,” said Barile. “Chris started making so much money he dropped out of school. That was a ‘holy shit’ moment. He can make a lot of money doing this and he’s doing a really good thing.”

The problem, said Barile, was safety. “He’s got all these devices he’s acquiring paying cash for and he’s driving all around town… Everyone who works in the [refurbish and resell] industry has at least one story about getting robbed at gunpoint.”

Backflip solved that problem by being the intermediary between buyers and sellers and taking a small commission for managing the transaction.

The company raised its first money at the end of 2019, but before that, Foosaner and Barile lived off of credit and used electronics.

So far, Backflip has facilitated the exchange of roughly 3,000 devices. The company handles everything from wiping a device and ensuring its quality to finding a buyer for the electronics. The company pays out roughly $150 per device and has deposited a little over $500,000 with users of the service, according to data provided by the company.

“We did all sorts of stuff to get our first few users,” said Barile. We posted ads on Facebook Marketplace and Craigslist. We started experimenting at the end of the summer with the most bare-bones mobile app kind of thing. At that point it was just Adam and I,” Barile said.

Starting now, Backflip is working with UPS stores to provide in-person drop-off and packaging centers for the used electronics. Over time, Barile sees those services expanding to offer cash on delivery. “The experience will be similar to an Amazon return,” he said. “Except we’ll be paying you.”

Currently about half of the company’s inventory is used handsets and mobile devices, but Barile said that could drop to a third of inventory as word spreads about the hundred-odd pieces of electronics that Backflip is willing to accept.

“Unlike other resale options, Backflip prioritizes the user’s time and convenience,” said Foosaner in a statement. “Forget the back-and-forth of negotiating over price and scheduling a meetup. We’re here to do all the work for the seller and make sure they get paid fairly and quickly. Backflip users can know that they’re getting the most for their devices without having to do anything other than bring them to The UPS Store or box them up at home.”

The connection to the refurbishing community started early for Barile, whose mother had a side business called “Stone Cottage Workshop” where she was flipping refurbished furniture on eBay and at local thrift stores near Barile’s bucolic New Jersey hometown.

“We want to build the Amazon of making things disappear from your apartment,” Barile said. 

Ten global startups, three rounds of pitching, nine expert judges. It’s not the 12 Days of Startups (no robotic partridge in a pear tree here), it’s the TC Early Stage Pitch-Off — otherwise known as day two of TC Early Stage 2021: Operations & Fundraising.

Yesterday on day one, TC Early Stage was all about invaluable how-tos. Today, it moves into a full day of action. TechCrunch vetted hundreds of applications to pitch at Early Stage 2021. Now it’s finally time for the epic battle, as these 10 exceptional startups throw down their best pitch — streamed live to a global audience including investors, press and tech industry leaders.

Each startup gets five minutes to pitch followed by a Q&A with their judges. The action kicks off at 9 a.m. PT with five startups participating in round one — Clocr, Crispify, Pivot Market, hi.health and Fitted.

They’ll have to bring the heat to impress their panel of VC judges: Marlon Nichols (co-founder and managing general partner at MaC Venture Capital), Sarah Smith (partner at Bain Capital Ventures) and Leah Solivan (general partner at Fuel Capital).

Round two begins at 10 a.m. PT and features FLX Solutions, Nalagenetics, The Last Gameboard, Attention Quotient and Soon. They’ll present their pitches to Lucy Deland (partner at Inspired Capital Partners), Eghosa Omoigui (founder and managing general partner at EchoVC Partners) and Neal Sáles-Griffin (managing director at Techstars).

Only three startups will make it into the final round, which starts at 11 a.m. PT. The finalists pitch yet again — facing a new panel of judges and a more extended Q&A. Who’s judging that final round? We tapped Wen Hsieh (partner at Kleiner Perkins), Natalie Sandman (partner at Spark Capital) and Stephanie Zahn (partner at Sequoia Capital).

Then it all comes down to one standout startup. Along with global exposure, the ultimate winner receives a feature article on TechCrunch.com, a free, one-year membership to Extra Crunch and a free Founder Pass to TechCrunch Disrupt 2021 in September.

Don’t forget the value of watching other startups pitch — and hearing the questions the judges ask them. Expert pitch feedback is invaluable, and you might just hear a few tips you can roll into your own presentation.

Ashley Barrington, founder of MarketPearl, experienced a variation on that theme at TC Early Stage 2020.

The Pitch Deck Teardown was incredibly helpful. Hearing the investors give feedback based on their perceptions and what they look for is so valuable. And seeing the other pitch decks and how different founders presented information was both interesting and informative.

Day two of TC Early Stage 2021 will be nonstop pitch action. Grab some popcorn, get comfy on the couch and tune in to the TC Early Stage Pitch-Off — the pitch you improve could be your own.

Updated 4/2/2021: Modified to reflect all pitch-off companies.

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Next Insurance recently announced that it has raised a $250 million round, valuing the SMB-focused insurance provider at $4 billion. The company last raised another $250 million in September 2020, at a valuation of $2 billion. This funding also comes after Next Insurance acquired Juniper Labs in December, and AP Intego more recently.

Next sells small-business coverage across a number of categories (workers’ comp, commercial auto, general liability, etc.) for different classes of workers. Think fitness companies, or construction concerns. Put together, Next’s bet is that its ability to price coverage across different categories and industries will allow it to scale its gross written premium (GWP) quickly by attracting myriad small businesses, and upselling them to other products over time.

Next Insurance’s new round and new valuation come at an interesting time for the insurtech space more broadly. Some air has come out of Lemonade’s share price, the rental-insurance unicorn being an early public debut for the broader tech-enabled, neo-insurance niche.

Since Lemonade’s debut, we’ve seen Root Insurance go public as well. The car insurance tech startup has struggled since its debut, losing value and attracting lawsuits despite besting investor growth expectations. MetroMile, another neo-insurance company focused on automotive that went public via a SPAC-led combination, has been slightly uneven since starting to trade. Hippo, which focuses on home insurance, intends to list via a SPAC itself at a $5 billion valuation.

Inside those numbers you can find optimism, and some lackluster trading results. How to parse the mix will depend on one’s perspective.

For Next Insurance’s backers, however, it’s all systems go. And there’s reason to believe that their enthusiasm is not misplaced, despite some chop in Next’s broader market.

Next says its GWP doubled in the half-year after its last round. That makes its valuation doubling seem somewhat reasonable — if private investors were willing to pay for its shares at a certain GWP multiple, why not re-up at double the price and double the GWP while the company continues to scale?

Just how big is Next today? It reached a GWP run rate of $100 million back in February of 2020. And it reached a $200 million GWP run rate in February of this year. So, larger than that by a few months’ growth, exclusive of the AP Intego business, which had around $185 million in active premium around the time its deal with Next Insurance was announced.

To clarify the numbers, TechCrunch reached out to Next Insurance for detail on when it doubled its GWP, and when the AP Intego deal started to count toward its numbers. Per an email from CEO Guy Goldstein, the doubling metrics regarding GWP was “in relation to that 2020 figure and [was calculated] before the AP Intego acquisition.” So, we can presume that the firm is now well north of the $200 million GWP run rate that it had previously cited.

Finally, TechCrunch asked the company about the SPAC boom and if it intended to avoid that rapid path to the public markets. “We’re always evaluating our options, but right now, the main focus remains on growing the business,” Goldstein responded.

That’s a no.

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Mexico has been known as an up-and-coming tech hub and a gateway to the Latin American market. As an investor focused on developer-centered products, open-source startups and infrastructure technology companies with a particular interest in emerging market innovation, I have been wanting to do some firsthand learning there.

So, despite the ongoing pandemic, I took all the necessary precautions and spent roughly seven weeks in Mexico from January to March. I spent most of my time meeting founders to get a handle on what they are building, why they are pursuing those ideas, and how the entire ecosystem is evolving to support their ambitions.

The U.S.-Asia-LatAm nexus

One fascinating, though not surprising, observation was how much LatAm entrepreneurs look to Asian tech giants for product inspiration and growth strategies. Companies like Tencent, DiDi and Grab are household names among founders. This makes sense because the market conditions in Mexico and other parts of LatAm resemble China, India and Southeast Asia more than the U.S.

What often happens is entrepreneurs first look to successful startups in the U.S. to emulate and localize. As they find product-market fit, they start to look to Asian tech companies for inspiration while morphing them to suit local needs.

One good example is Rappi, an app that started out as a grocery delivery service. Its future ambition is squarely to become the superapp of LatAm: It is expanding aggressively both geographically and productwise into delivery for restaurant orders, pharmacy and even COVID tests. It’s also introducing new payment, banking and financial-service products. Rappi Pay launched in Mexico just a few weeks ago, while I was still in the country.

Rappi now looks more like Meituan and Grab than any of its U.S. counterparts, and that’s not an accident. SoftBank, whose portfolio contains many of these Asian tech giants, invested heavily in Rappi’s previous two rounds and now has a $5 billion fund dedicated to the LatAm region. The knowledge and experience accumulated from Asian tech in the last 10 years is transferring to like-minded firms like Rappi, right under Silicon Valley’s proverbial nose.

U.S.-Asia-LatAm competition

Knowledge transfer is not the only trend flowing in the U.S.-Asia-LatAm nexus. Competition is afoot as well.

Because of similar market conditions, Asian tech giants are directly expanding into Mexico and other LatAm countries. The one I witnessed up close during my visit was DiDi.

DiDi’s foray into LatAm started in January 2018 with its acquisition of 99, a Brazilian ride-sharing company. In April 2018, DiDi entered Mexico with its bread-and-butter ride-sharing service. It wasn’t until April 2019 that DiDi launched its food delivery service, DiDi Food, in Monterrey and Guadalajara — two of the largest cities in Mexico. Its expansion hasn’t slowed down since, with a 10% extra earnings incentive to lure delivery drivers.

My Airbnb in Mexico City happened to be two blocks away from the large WeWork building where DiDi’s local office was located. Every day, I saw a long line of people responding to the earning incentives — waiting outside to get hired as DiDi delivery workers.

Meanwhile, the Uber office that’s literally one block away had hardly any foot traffic. As Uber and Rappi fight for more wealthy consumers, DiDi is working to attract lower-income users to grab market share, hoping that one day some of these people will reach the middle class and become profitable customers.