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Welcome back to The TechCrunch Exchange, a weekly startups-and-markets newsletter. It’s broadly based on the daily column that appears on Extra Crunch, but free, and made for your weekend reading.

Well that was a crazy week

I may be getting older, but it does seem that the pace of tech news has gotten stuck in top-gear. It’s bonkers. Think about how small a splash the news that WeWork is going public via a SPAC made. It was small potatoes in the broader rush of happenings that blasted past us over the last seven days.

Y Comabinator’s Demo Day was this week, somehow, even if it feels like a few weeks have gone by since. Still, it’s what I want to riff on with you today. A nice early-stage break, we could say.

During the one-day demo day rush, a few hundred startups showed off what they are doing in single-slide format. TechCrunch covered some favorites, but we had to leave far more startups on the shelf than we got to write about. Let’s add some names to the mix, shall we?

On the fintech front, a few names stood out to me during the hours I was able to tune in. Alinea wants to build a trading app for Gen Z. I dig the idea as Zoomers seem far cooler than any other generation. Why shouldn’t they get a native investing experience aimed at their demographic?

Hapi is a similar idea, but aimed at Latin America. Again, I like it. One trend I’ve enjoyed seeing in recent quarters has been the application of startup models that have worked in the United States taken to new markets, replicated with local tweaks, and offered up to way more people. Investing has long been artificially expensive. Here’s to making it cheaper.

Atrato checks similar boxes, taking the Affirm-style buy now, pay later (BNPL) model to Latin America. I am generally less stoked about consumer credit apps than I am about consumer savings apps, but given the growth that Affirm, Klarna and others have managed, there’s real demand for their products. Let’s see what Atrato can get done.

Turning from Latin America to Southeast Asia, OctiFi is building BNPL products for that market. It’s not the only startup that we saw at demo day taking on that geographic slice — BrioHR is working there as well.

Bueno Finance fits the theme of fintech for markets other than the United States and Europe, building what it calls “Chime for India.” If you think, as I do, that Chime and other neobanks are generally doing an alright job providing lower-cost, higher-quality banking experiences to less-wealthy consumers, this is an obvious winner. Of course most startups fail, but I like where their thinking is focused. (NextPay is working on SMB digital banking for the Philippines; the list goes on.)

Another theme I had my eyes on were startups delivering their software via an API instead of as a managed service. It’s something that we’ve covered on The Exchange for ages. Some demo day names included Dyte (“Stripe for live video”), Pibit.ai (an API to help structure data), Dayra (finservices for Egyptians via an API), enode (energy provider-EV API), and so on.

Finally, there were a few startups working on services for IRL SMBs. The Third Place is building subscription services for small businesses, while Per Diem wants to bring quick shipping to companies other than Amazon.

There were a bunch of other neat companies (GimBooks! Recover! Wasp! Axiom.ai!), more than I could ever write down for you. Now it’s time to sit back and see which grow the most in the next half year. But I left this particular demo day pretty excited about global startup activity. That’s not a bad way to close a Tuesday.

Late-stage everything

Amidst all the IPO and SPAC news (here and here in case you need to catch up), there were a host of big rounds worth our time. Two came from the insurtech space, with Pie (workers’ comp insurance) and Snapsheet (claims management) raising $118 million and $30 million apiece.

ServiceTitan raised $500 million at a quadrupled valuation of $8.3 billion, Forbes reported. In about two years. That’s a chonky boi valuation differential. I suppose we’ll be covering their IPO next year. And accounting-focused Pilot raised $100 million at a $1.2 billion valuation. The pace of 2021 unicorn creation feels anything but slow.

And I can’t help but note that the UiPath IPO filing is pretty bonkers in terms of illustrating how the company turned terrifying losses into some pretty reasonable economics. It’s looking like it’s working to pull a Snowflake, at least in GAAP terms.

I could add another 17 paragraphs with news just from this month and not even get close to all the eight and nine-figure rounds. It’s bonkers! Surely the Q1 2021 venture capital numbers feel like they should be both hot and spicy. More on that as soon as we get the data.

Various and sundry

I am not here to merely feed you vegetables, however. There’s a budding story that I need to get to in the near future that involves my favorite sport, and my job. More precisely it’s about F1 (the car racing thing) and tech.

Recently Cognizant sponsored the Aston Martin F1 team. Splunk works with McLaren. Microsoft has a deal with Renault’s team, now named after the car company’s Alpine brand. Epson, Bose and Hewlett Packard Enterprise sponsor the Mercedes racing team. Oracle sponsors Red Bull racing. The list goes on!

And this week Zoom announced that it was getting into the F1 game as well. This is all very good fun for myself, and leads me to a hope. Namely that we see some tech companies begin to use F1 teams as a method of intra-industry competition. That would, one, allow me to write about F1 at work — like I am doing right now — and annoy more tech CEOs on earnings calls about why their team isn’t faster. I am sure that by now Splunk CEO Douglas Merritt is tired of my questions about his orange team. But I don’t want to stop.

So if you are a tech CEO, and you do not sponsor an F1 team, I shall from here on presume that your company is too small to matter, or too boring to be fun. And I am only mostly kidding.

Alex

Within 48 hours, the startup world experienced two momentous events: Y Combinator’s largest Demo Day ever, and the early investor exodus of Dispo, a photo-sharing app. Both events, while seemingly unrelated, taught us a lot about the importance, and difficulty, of due diligence in our current world.

For background, early investors in Dispo distanced from the startup after a key investigation unearthed allegations around co-creator and popular YouTuber, David Dobrik. Per venture capitalists I spoke to, the move to “sever all ties” with Dispo was unprecedented.

• Spark Capital decides to ‘sever all ties’ with David Dobrik’s Dispo app weeks after leading deal
• Early investors in Dispo to donate any potential profits from the photo-sharing app

So what’s the impact here? It’s a rude awakening on the importance of due diligence. On Equity, I argued that the Dispo news should nudge venture capitalists to do a more thorough job with vetting founders in the future. Dobrik’s questionable “pranks” were always a search away.

Even though one person doesn’t represent an entire company (Dispo’s team seems great, for what it’s worth), investors still left because of what their money represented. Fast forward, this event could have a chilling effect on VCs working with celebrities or influencers. The liability just seems too huge to back a startup led by potentially problematic individuals, so either stay away or do your homework.

Well, you’d think. Ironically, 24 hours after Dispo investors backed away from the startup was YC Demo Day, one of the marquee startup events of the year. My colleague joked that founders don’t simply need to figure out how to get into Y Combinator anymore — they need to figure out how to stand out in the batch once they get there. The comment, made in jest, underscored a truth about the current startup funding environment: too noisy to handle.

• Our favorite companies from Y Combinator’s W21 Demo Day: Part 1
• Our favorite companies from Y Combinator’s W21 Demo Day: Part 2
• Y Combinator’s new batch features its largest group of Indian startups
• Y Combinator widens its bet in edtech in latest batch
• Y Combinator’s biotech startups incubate a new generation of therapies and tools

Noise turned into free-for-all investments. One investor got an email from a batch company saying essentially, “thanks for your interest, if you want to invest here’s a document, no due diligence required.” The startup was valued at $100 million. Another investor I spoke to said that a company asked for an investment without meeting the VC.

While these are only anecdotes, I think these pitches are illustrative of the disconnect between the importance of due diligence and the hype cycle we are in. As Dispo showed us, it’s net positive to vet your future partner, back the right startups and bring on the right money. As YC Demo Day showed us, it’s hard to go slow when you can go fast. If the money is dangling in front of you, how do you say no?

• Pre-seed funding is under scrutiny, is VC pandemic-posturing here to stay?https://twitter.com/pjux/status/1374805872371666948
• You can only invest if you promise not to read the fine print, ok?

I don’t have a solution to the disconnect, and ultimately the change comes down to the ethos of individual investors and founders. But at minimum, this week of extremes gives a dose of reality to startup mania right now.

In the rest of this newsletter, we’ll focus on a five-month unicorn, and Plaid’s harmony at Discord’s cost. As always, you can find me on Twitter @nmasc_. 

Image Credits: Getty Images

‘From launch to unicorn in 5 months’

Pacaso, a startup that wants to make it easier for people to have second home ownership, has reached a $1 billion valuation in just five months. The startup essentially wants to reinvent timeshares, with the goal of “bringing together a small group of co-owners to purchase a share of a single-family home” with access throughout the year, Mary Ann Azevedo reports.

You can get Startups Weekly in your inbox every Saturday, so subscribe here to join the cool kids. 

Here’s what to know: The proptech unicorns are here to stay. My colleague Eric Eldon wrote about real estate trends, from co-living to a suburban-style living boom.

• And if you don’t believe us: In this latest investor survey, Eldon surveyed 10 proptech investors who see a better era for residential and retail after the pandemic.

Colorful bar and light trails composed on the collaged circuit boards. It’s images of big data in Cyber City. Image Credits: Hiroshi Watanabe / Getty Images

Exits, and Plaid’s lack thereof

Even an ol’ enterprise giant wants to remind you that community matters. Microsoft is reportedly trying to scoop up Discord, in deal talks that would value the latter at $10 billion. The startup was last valued at $7 billion.

Here’s what to know: The deal price feels slightly cheap, argues the Equity trio. When you consider the fact that Plaid could be valued at almost double or triple for what it was going to be sold to Visa, one has to wonder if Discord has an anti-trust discount limiting its pricing.

• Speaking of legal headaches: Robinhood filed confidently to go public, which, sue me, makes me excited as heck!
• Coursera set to roughly double its private valuation in impending IPO

Image Credits: Discord

Around TechCrunch

• Here’s a discount code to our TechCrunch Early Stage conference, our two-day virtual event for founders, investors and operators. Use code “TCARTICLE” to get 20% off your ticket so you can attend super-cool events like how to bootstrap with Calendly’s Tope Awotona and OpenView’s Blake Bartlett, how to pitch your Series A fundraise with Kleiner Perkins’ Bucky Moore (moderated by moi) and finance for founders with Alexa von Tobel.
• Grab super early-bird passes to TechCrunch Disrupt for less than $100. Equity might do something fun and special, who knows.
• The TechCrunch List is a directory of the most active and engaged investors in the VC industry today as recommended by founders.

Across the week

Seen on TechCrunch

Elon Musk declares you can now buy a Tesla with bitcoin in the US

Slack’s new DM feature Connect is thankfully opt-in

The Frankencloud model is our biggest security risk

As more artists and musicians turn their attention to NFTs, so, likely, do money launderers

Tableau CEO Adam Selipsky is returning to AWS to replace Andy Jassy as CEO

Seen on Extra Crunch

It’s time to abandon business intelligence tools

NFTs could bridge video games and the fashion industry

How VC and private equity funds can launch portfolio-acceleration platforms

Steady’s Adam Roseman and investor Emmalyn Shaw outline what worked (and what was missing) in the Series A deck

Who knew building a vertical software as a service toolkit focused on home heating and cooling could be worth $8.3 billion?

That’s how much Los Angeles-based ServiceTitan, a startup founded just eight years ago is worth now, thanks to some massive tailwinds around homebuilding and energy efficiency that are serving to boost the company’s bottom line and netting it an unprecedented valuation for a vertical software company, according to bankers.

The company’s massive mint comes thanks to a new $500 million financing round led by Sequoia’s Global Equities fund and Tiger Global Management.

ServiceTitan’s backers are a veritable who’s who of the venture industry, with longtime white shoe investors like Battery Ventures, Bessemer Venture Partners and Index Ventures joining the later stage investment funds like T. Rowe Price, Dragoneer Investment Group, and ICONIQ Growth.

In all, the new $500 million round likely sets the stage for a public offering later this year or before the end of 2022 if market conditions hold.

ServiceTitan now boasts more than 7,500 customers that employ more than 100,000 technicians and conduct nearly $20 billion worth of transactions providing services ranging from plumbing, air conditioning, electrical work, chimney, pest services and lawn care.

If Angi and Thumbtack are the places where homeowners go to find services and technicians, then ServiceTitan is where those technicians go to manage and organize their own businesses.

Based in Glendale, Calif., with satellite offices in Atlanta and Armenia, ServiceTitan built its business to solve a problem that its co-founders knew intimately as the children of parents whose careers were spent in the HVAC business.

The market for home services employs more than 5 million workers in the US and represents a trillion dollar global market.

Despite the siren song of global expansion, there’s likely plenty of room for ServiceTitan to grow in the U.S. Home ownership in the country is at a ten-year high thanks to the rise of remote work and an exodus from the largest American cities accelerated by the COVID-19 pandemic.

A focus on energy efficiency and a desire to reduce greenhouse gas emissions will likely cause a surge in residential and commercial retrofits which will also boost new business. Indeed these trends were already apparent in the statistic that home improvement spending was up 3 percent in 2020 even though the broader economy shrank by 3.5 percent.

One of the biggest pain points for startups and small businesses is keeping up with back office tasks such as bookkeeping and managing taxes.

QuickBooks, it seems, just doesn’t always cut it.

Three-time co-founders Waseem Daher, Jeff Arnold, and Jessica McKellar formed Pilot with the mission of affordably providing back office services to startups and SMBs. With over 1,000 customers, it has gained serious traction over the years. And Pilot has now also received validation from some big-name investors. On Friday, the company announced a $100 million Series C that doubles the company’s valuation to $1.2 billion.

Bezos Expeditions — Amazon founder Jeff Bezos’ personal investment fund — and Whale Rock Capital (a $10 billion hedge fund) co-led the round, which also included participation from Sequoia Capital, Index Ventures, Authentic Ventures and others. 

Stripe and Index Ventures co-led Pilot’s $40 million Series B in April 2019. The latest financing brings the company’s total funding raised to over $158 million since its 2017 inception.

The founding team certainly has an impressive track record, having founded and sold two previous companies: Ksplice  (to Oracle) and Zupli (to Dropbox).

Pilot’s pitch is about more than just software. The company combines its software with accountants to do things such as provide “CFO Services” to SMBs without a full-stack finance team. It also provides monthly variance analysis for all its bookkeeping customers, essentially serving as a controller for those companies, so they can make better budgeting and spending decisions.

It also helps companies access small business tax credits they may not have otherwise known about. 

Last year, Pilot completed more than $3 billion in bookkeeping transactions for its customers, which range from pre-revenue startups to larger companies with more than $30M of revenue a year. Customers include Bolt, r2c and Pathrise, among others.

Pilot has also inked a number of co-marketing partnerships with companies such as American Express, Bill.com, Brex, Carta, Gusto, Rippling, Stripe, SVB, and Techstars.

Ironically, Pilot says it aspires to the “AWS of SMB backoffice.” (In fact, co-founder Waseem Daher started his career as an intern at Amazon). Put simply, Pilot wants to take care of all those back office tasks so companies can focus more on growth and winning business.

Pilot strives to offer an “exceptional customer experience,” which is reflected in the fact that over 80% of the company’s business is driven by customer referrals and organic interest, according to Daher.

Whale Rock Partner Kristov Paulus said that white-glove customer service experience and Pilot’s “carefully-engineered” software make a powerful combination.

“We look forward to supporting Pilot in their vision to make back office services as easy-to-use, scalable, and ubiquitous as AWS has with the cloud,” he said.

Pilot’s model reminds me a lot of that of ScaleFactor’s, an Austin-based startup that raised $100 million in a year before it crashed and burned. But the difference in this case is that Pilot seems to have satisfied customers.

Mayfield partner Navin Chaddha and Poshmark founder and CEO Manish Chandra met all the way back in 2003, well before Poshmark was even a glimmer in his eye. They stayed connected over the years, through Chandra’s sale of his startup Kaboodle to Hearst and after he left.

At a breakfast one morning, Chandra told Chaddha he was going to try to do everything from his iPhone for the next six months.

Over the course of that time, the idea for Poshmark started to percolate into something more concrete. Chandra, following Kaboodle, knew he wanted to do several things differently. The first was create an engagement and revenue model that was symbiotic, rather than starting with engagement and having to build out a business model later. He also knew he wanted to start with people first, and build a founding team that had deep DNA in the fashion world to pair with his technical background.

He met Tracy Sun, brought her on, and got to work.

This was back in 2011, and Chandra was absolutely adamant that he wanted Poshmark to be an app, not a website. So adamant, in fact, that during beta he actually provided 100 users with video iPods. (He recalled that he only got 20% of them back.)

“Lead with love, and the money comes.” It’s one of the cornerstone values at Poshmark. The company practiced that early on by holding IRL, and then virtual, parties, allowing users to show each other their wares and create an engagement cycle that offered instant gratification. The user base grew from 100 to 150 to 1,000 and so on.

“We still to this day use a similar kind of strategy in a much more compressed timeframe as we go to different countries,” said Chandra. “We focus on building the community first and then scale that community.”

Chaddha and Mayfield led the company’s Series A deal a decade ago. On the latest episode of Extra Crunch Live, Chandra and Chaddha sat down with us and walked us through that original Series A pitch deck (which you can check out below). They also participated in the Pitch Deck Teardown, giving their expert feedback on decks submitted by the audience. If you’d like your deck to be featured on a future episode of Extra Crunch Live, hit up this link.

Poshmark’s Series A Deck

Time stamp — 11:00

Poshmark was built on a couple fundamental premises. The first was that the iPhone would transform the way we do just about everything. The second was more pointed: That fashion, at the time underserved by technology, was a discovery process over a direct search process. A decade ago, Chandra envisioned a fashion marketplace that mimicked shopping in the real world — walk into a shop and let natural attraction do its thing — without holding any inventory.