Khosla Ventures
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More than five years ago, Sequoia partner Alfred Lin called Tony Xu, the founder of a small on-demand delivery startup called DoorDash, to say he was passing on the company’s seed round.
This was, of course, before venture capital funding in food delivery startups had taken off. DoorDash, launched out of Xu’s Stanford graduate school dorm room, wasn’t worth Sequoia’s capital — yet.
Today, venture capitalists are valuing the San Francisco-based company at a whopping $12.6 billion with a $600 million Series G. New investors Darsana Capital Partners and Sands Capital participated in the deal, which nearly doubles DoorDash’s previous valuation, alongside existing backers Coatue Management, Dragoneer, DST Global, Sequoia Capital, the SoftBank Vision Fund and Temasek Capital Management.
As for Sequoia’s Alfred Lin, he realized his mistake years ago and jumped in on DoorDash’s 2014 Series A, and has participated in every subsequent round since. DoorDash, a graduate of Y Combinator’s Summer 2013 cohort, is also backed by Kleiner Perkins, CRV and Khosla Ventures, among others. In total, the company has raised $2.5 billion in VC funding, making it one of the most well-capitalized private companies in the U.S.
SoftBank, via its prolific dealmaker Jeffrey Housenbold, was responsible for making DoorDash a unicorn in early 2018. The nearly $100 billion Vision Fund led DoorDash’s $535 million Series D, valuing the business at $1.4 billion. Just three months ago, the SoftBank Vision Fund, DST Global, Coatue Management, GIC, Sequoia and Y Combinator put an additional $400 million in the fast-growing business.
SAN FRANCISCO, CA – SEPTEMBER 05: DoorDash CEO Tony Xu speaks onstage during Day 1 of TechCrunch Disrupt SF 2018 at Moscone Center on September 5, 2018 in San Francisco, California. (Photo by Kimberly White/Getty Images for TechCrunch)
Xu told TechCrunch the company’s Series F was “a reflection of superior performance over the past year.” DoorDash was currently seeing 325% growth year-over-year, he said, pointing to recent data from Second Measure showing the service had overtaken Uber Eats in the U.S., coming in second only to GrubHub.
“I think the numbers speak for themselves,” Xu said at the time. “If you just run the math on DoorDash’s course and speed, we’re on track to be number one.”
At a venture capital-focused summit hosted in April, Xu added that DoorDash was the largest delivery platform in America by “pretty wide margins,” explaining that it was, in fact, growing 4x faster than its next closest peer. In this morning’s announcement, the company added that it’s grown 60% since its late February Series F, with its annualized total sales hitting $7.5 billion in March, an increase of 280% year-over-year.
Still, one wonders what kind of growth metrics DoorDash might be sharing to attract that kind of valuation multiple. The company has yet to disclose revenues and is not yet profitable, but has seen its price tag grow astronomically in just two years. Since March 2018, DoorDash’s valuation has skyrocketed from $1.4 billion to $4 billion with a $250 million Series E to $7.1 billion with a $350 million Series F and, finally, to nearly $13 billion with its Series G.
The $12.6 billion valuation makes DoorDash one of the 10 most valuable venture-backed companies in the U.S., surpassing Coinbase, Instacart and even Slack, according to PitchBook.
DoorDash is currently active in more than 4,000 cities in the U.S. and Canada, with hundreds of partners, including both restaurants and supermarkets (Walmart is using DoorDash for grocery deliveries). The company also operates DoorDash Drive, which allows businesses to use the DoorDash network to make their own deliveries.
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The enterprise software and services-focused accelerator Alchemist has raised $4 million in fresh financing from investors BASF and the Qatar Development Bank, just in time for its latest demo day unveiling 20 new companies.
Qatar and BASF join previous investors, including the venture firms Mayfield, Khosla Ventures, Foundation Capital, DFJ and USVP, and corporate investors like Cisco, Siemens and Juniper Networks.
While the roster of successes from Alchemist’s fund isn’t as lengthy as Y Combinator, the accelerator program has launched the likes of the quantum computing upstart Rigetti, the soft-launch developer tool LaunchDarkly and drone startup Matternet .
Some (personal) highlights of the latest cohort include:
Watch a live stream of Alchemist’s demo day pitches, starting at 3PM, here.
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Daye, a “femcare” startup developing a new type of tampon that uses CBD to help tackle dysmenorrhea, has quietly raised $5.5 million in funding from high-profile investors in the U.S. and Europe, TechCrunch has learned.
Backing the seed round is Silicon Valley’s Khosla Ventures, along with London’s Index Ventures and Kindred Capital. The investment sees Khosla’s chief of staff Kristina Simmons, Khosla venture partner Tim Westergren (who also founded Pandora), and Hannah Seal, principle at Index, join Daye’s board.
Other investors in the London-based company include Sophia Bendz (former global director of Marketing at Spotify and now a partner at VC firm Atomico), Irina Havas (a principle of Atomico), David Schiff (founding partner at United Talent Agency) and Kristin Cardwell (VP of International Business Development at Refinery29).
Founded by 24-year-old Valentina Milanova and launching later this year, Daye has set out to build a new brand for female health products “designed with women in mind.” The startup’s first product is a newly developed tampon that uses CBD to help tackle period cramps (or dysmenorrhea) as an alternative to traditional painkillers (CBD is the extract derived from the flower of the industrial hemp plant, a legal relative to marijuana). Daye also claims its product will be more hygienic and sustainable than legacy tampons, and if successful could be a wake-up call to the incumbent and stagnant tampon industry, which has seen little innovation in decades.
“Our goal is to raise the standards of women’s hygiene products by tackling three primary issues: dysmenorrhea, manufacturing standards and sustainability,” Milanova tells TechCrunch. “Women have largely been left out of medical innovation. In fact, until 1993, researchers banned women from participating in [early] clinical trials, as it was believed female hormone fluctuations polluted medical data. To this day, most medications, including those for pain relief, depression and sleeping aids, have not been tested on women. We’re redefining localised cramp-relief, relying on an ingredient that we’ve tested on women first.”
Milanova says she first had the idea for a cramp-fighting tampon in November 2017 and initially used her salary from a day job and credit cards to fund product development. In September 2018, she quit her job to work on the business full-time and build a team, and to finalise clinical trials for the product.
Describing CBD as “having its 15 minutes of fame,” Milanova says the company doesn’t believe cannabidiol should be added to everything, from dry shampoo to cocktails. However, she says CBD is much safer than over-the-counter painkillers, and that the vaginal canal has the highest concentration of cannabinoid receptors and is also the fastest route of absorption into the bloodstream when it comes to pain relief.
“Unlike most CBD products on the market today, our product does not contain any tetrahydrocannabinol (THC),” she explains. “This is why we believe we’re going to be attractive to every consumer who experiences menstrual discomfort.”
Beyond the novel idea of a cramp-fighting CBD tampon, Milanova says Daye wants to raise the bar for tampon production standards and sustainability.
“In Europe, tampons are not classified as medical devices, which means there are no manufacturing guidelines — for context, plasters are more regulated and better sanitised than tampons,” she tells me, to my astonishment. To address this, Daye is introducing pharmaceutical-grade standards and will keep manufacturing in-house.
Period care is also “wreaking havoc” on the environment. “Over the course of her lifetime, the average woman uses enough tampons to fill two double-decker buses. That waste either ends up in our oceans or landfills. We want to relieve the burden period care has on the environment, and offer a product that is equal parts body-safe, effective and as sustainable as possible.”
To begin to answer the question of why something like this hasn’t been done before, Milanova says that menstrual discomfort in general is a massively overlooked problem and that “even the mention of the word tampon makes most people feel uncomfortable.”
The existing market is also monopolised “to the point where innovation suffers.” All tampons on the market today perform and look the same, using the same materials and the same manufacturing processes. Yet, because there’s barely any product differentiation, the Daye founder says most women remain loyal to the first tampon brand they ever tried.
“What we’re bringing to market is a completely novel product, and we’re operating in a very sensitive, intimate area of consumer goods. As a newcomer, we have to gain consumer trust by ensuring we’re in constant contact with our users, taking note of their feedback and iterating on our proposition fast.”
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In Riga, Latvia, an 80-person startup called Printify is reimagining the on-demand printing business.
Gone are the days where small merchants have to sell their customized products on platforms like Zazzle, Society6, CafePress or Teespring . Using Printify, e-commerce business owners can create clothes, accessories and more fixed with their designs, logos, art or photos, then sell them directly on their very own online stores.
The “first wave” of on-demand printing companies, Printify founder and chief executive officer James Berdigans explained to TechCrunch, typically require that merchants sell their items on the provider’s platforms.
“The problem is that these merchants don’t have the capability to build their own brand,” Berdigans said. “At the end of the day, you end up building the Teespring brand, not your own brand.”
Printify, a graduate of the 500 Startups accelerator, has attracted a $3 million investment from Bling Capital, a venture capital fund launched five months ago by Ben Ling, a former general partner at Khosla Ventures.
“Printify is perfectly positioned to enable the new trend of micro and boutique brands,” Ling said in a statement. “Consumers and SMBs alike can benefit from Printify’s high-quality, low-cost and fast printing platform — and create their own micro-brands.”
Founded in 2015 by Berdigans, Artis Kehris and Gatis Dukurs, Printify had previously raised a $1 million round following a big pivot. Initially, the business “pretended to be the manufacturer,” opting to be less transparent as a means to entice customers.
“That was a terrible idea,” Berdigans said. “Even though you aren’t lying, you end up not being a very honest company and that’s not the business model we wanted.”
Now, Printify operates as a B2B marketplace that connects manufacturers with e-commerce stores. Plus, the startup handles the mundane tasks of fulfilling orders, including billing, manufacturing requests and shipping so store owners can focus on brand building. The switch allowed the startup to begin growing 30% month-over-month, as well as add hundreds of unique products to its catalog.
The founders say Printify most often caters to political campaign employees, designers & artists, and influencers & “hustlers,” or people who are self-taught experts on managing digital sales. With a fixed pricing scheme, merchants know exactly what they are paying Printify, but have the flexibility of pricing their own product. Other print-on-demand marketplaces, like the aforementioned “first wave” businesses, don’t give merchants the ability to determine their own margins.
“If you use Zazzle, for example, you only get a small portion of revenue share but on Printify, you pay us a small fee,” Berdigans said. “If you were selling t-shirts for $25 and the average production cost is $10, our sellers will see a 50 to 60% margin.”
Dozens of angel investors, including YouTube co-founder Steve Chen, Twitch co-founder Kevin Lin, ClassPass co-founder Fritz Lanman, DoorDash co-founder Evan Moore, Google AdSense pioneer Gokul Rajaram and Facebook’s vice president of product Kevin Weil, also participated in the company’s latest round.
“What Airbnb did for the hospitality industry, that’s basically what we can do for the print-on-demand industry,” said Kehris, Printify’s chief operating officer.
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Sam Altman’s little brother Jack is an entrepreneur, too.
Jack Altman, whose resume includes a stint as vice president of business development at Teespring, has raised $15 million in Series B funding for his startup, Lattice, a modern approach to corporate goal setting. Shasta Ventures led the round, with participation from Thrive Capital, Khosla Ventures and Y Combinator, the latter being the organization his brother led as president until very recently.
Lattice, used by high-growth companies like Reddit, Slack, Coinbase and Glossier, helps human resources professionals develop insights about their teams. Founded in 2015, Altman and Eric Koslow, like most entrepreneurs, developed the idea for Lattice out of their own pain points.
“We realized that with quarterly goal settings, OKRs, we would write them up and get the leadership together and then they would sit on a shelf and nothing would happen,” Altman told TechCrunch.
Lattice, a SaaS business, is a flexible platform that caters to startups and larger businesses’ specific cultures, management practices and varying approaches to employee engagement. The product, inspired by platforms like Gmail and Slack, is designed with consumers in mind. Lattice, the team hopes, has a look and feel that makes incumbent HR platforms feel antiquated.
The product makes it simple for employees and their managers to complete engagement surveys, share feedback, arrange one-on-one meetings and complete comprehensive performance reviews with a larger goal of reworking the company goal-setting process entirely. No more once-yearly check-ins; Lattice enables businesses to check-in with their employees on a weekly basis.
Lattice currently has 1,200 customers, 60 employees and was cash flow break-even for the first time in Q1 2019. With the latest financing, the San Francisco-based startup plans to invest in product development.
“Life is short,” Altman said. “You want to have work that you enjoy and an office that feels good to be at.”
Lattice has previously raised capital from investors including SV Angel, Marc Benioff, Slack Fund and Fuel Capital, Sam Altman, Elad Gil, Alexis Ohanian, Kevin Mahaffey, Daniel Gross and Jake Gibson. Lattice completed the Y Combinator startup accelerator in 2016.
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As I’m sure everyone reading this knows, female-founded businesses receive just over 2 percent of venture capital on an annual basis. Most of those checks are written to early-stage startups. It’s extremely difficult for female founders to garner late-stage support, let alone cash $100 million checks.
Maybe that’s finally changing. This week, not one but two female-founded and led companies, Glossier and Rent The Runway, raised nine-figure rounds and cemented their status as unicorn companies. According to PitchBook data from 2018, there are only about 15 unicorn startups with female founders. Though I’m sure that number has increased in the last year, you get the point: There are hundreds of privately held billion-dollar companies and shockingly few of those have women founders (even fewer have female CEOs)…
Moving on…

I spent a good part of the week at San Francisco’s Pier 48 in a room full of vest-wearing investors. We listened to some 200 YC companies make their 120-second pitch and though it was a bit of a whirlwind, there were definitely some standouts. ICYMI: We wrote about each and every company that pitched on day 1 and day 2. If you’re looking for the inside scoop on the companies that forwent demo day and raised rounds, or were acquired, before hitting the stage, we’ve got that too.
Lyft: This week, Lyft set the terms for its highly-anticipated initial public offering, expected to be completed next week. The company will charge between $62 and $68 per share, raising more than $2 billion at a valuation of ~$23 billion. We previously reported its initial market cap would be around $18.5 billion, but that was before we knew that Lyft’s IPO was already oversubscribed. Here’s a little more background on the Lyft IPO for those interested.
Uber: The global ride-hailing business flew a little more under the radar this week than last week, but still managed to grab a few headlines. The company has decided to sell its stock on the New York Stock Exchange, which is the least surprising IPO development of 2019, considering its key U.S. competitor, Lyft, has been working with the Nasdaq on its IPO. Uber is expected to unveil its S-1 in April.
Ben Silbermann, co-founder and CEO of Pinterest, at TechCrunch Disrupt SF 2017.
Pinterest: Pinterest, the nearly decade-old visual search engine, unveiled its S-1 on Friday, one of the final steps ahead of its NYSE IPO, expected in April. The $12.3 billion company, which will trade under the ticker symbol “PINS,” posted revenue of $755.9 million in the year ending December 31, 2018, up from $472.8 million in 2017. It has roughly doubled its monthly active user count since early 2016, hitting 265 million last year. The company’s net loss, meanwhile, shrank to $62.9 million in 2018 from $130 million in 2017.
Zoom: Not necessarily the buzziest of companies, but its S-1 filing, published Friday, stands out for one important reason: Zoom is profitable! I know, what insanity! Anyway, the startup is going public on the Nasdaq as soon as next month after raising about $150 million in venture capital funding. The full deets are here.
General Catalyst, a well-known venture capital firm, is diving more seriously into the business of funding seed-stage business. The firm, which has investments in Warby Parker, Oscar and Stripe, announced earlier this week its plan to invest at least $25 million each year in nascent teams.
Earlier this week, Opendoor, the SoftBank -backed real estate startup, filed paperwork to raise even more money. According to TechCrunch’s Ingrid Lunden, the business is planning to raise up to $200 million at a valuation of roughly $3.7 billion. It’s possible this is a Series E extension; after all, the company raised its $400 million Series E only six months ago. Backers of OpenDoor include the usual suspects: Andreessen Horowitz, Coatue, General Atlantic, GV, Initialized Capital, Khosla Ventures, NEA and Norwest Venture Partners.
Startup capital
Backstage Capital founder and managing partner Arlan Hamilton, center.
Axios’ Dan Primack and Kia Kokalitcheva published a report this week revealing Backstage Capital hadn’t raised its debut fund in total. Backstage founder Arlan Hamilton was quick to point out that she had been honest about the challenges of fundraising during various speaking engagements, and even on the Gimlet “Startup” podcast, which featured her in its latest season. A Twitter debate ensued and later, Hamilton announced she was stepping down as CEO of Backstage Studio, the operations arm of the venture fund, to focus on raising capital and amplifying founders. TechCrunch’s Megan Rose Dickey has the full story.
This week, TechCrunch’s Connie Loizos revisited a long-held debate: Pro rata rights, or the right of an earlier investor in a company to maintain the percentage that he or she (or their venture firm) owns as that company matures and takes on more funding. Here’s why pro rata rights matter (at least, to VCs).
If you enjoy this newsletter, be sure to check out TechCrunch’s venture-focused podcast, Equity. In this week’s episode, available here, Crunchbase News editor-in-chief Alex Wilhelm and I chat about Glossier, Rent The Runway and YC Demo Days. Then, in a special Equity Shot, we unpack the numbers behind the Pinterest and Zoom IPO filings.
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Hundreds gathered this week at San Francisco’s Pier 48 to see the more than 200 companies in Y Combinator’s Winter 2019 cohort present their two-minute pitches. The audience of venture capitalists, who collectively manage hundreds of billions of dollars, noted their favorites. The very best investors, however, had already had their pick of the litter.
What many don’t realize about the Demo Day tradition is that pitching isn’t a requirement; in fact, some YC graduates skip out on their stage opportunity altogether. Why? Because they’ve already raised capital or are in the final stages of closing a deal.
ZeroDown, Overview.AI and Catch are among the startups in YC’s W19 batch that forwent Demo Day this week, having already pocketed venture capital. ZeroDown, a financing solution for real estate purchases in the Bay Area, raised a round upwards of $10 million at a $75 million valuation, sources tell TechCrunch. ZeroDown hasn’t responded to requests for comment, nor has its rumored lead investor: Goodwater Capital.
Without requiring a down payment, ZeroDown purchases homes outright for customers and helps them work toward ownership with monthly payments determined by their income. The business was founded by Zenefits co-founder and former chief technology officer Laks Srini, former Zenefits chief operating officer Abhijeet Dwivedi and Hari Viswanathan, a former Zenefits staff engineer.
The founders’ experience building Zenefits, despite its shortcomings, helped ZeroDown garner significant buzz ahead of Demo Day. Sources tell TechCrunch the startup had actually raised a small seed round ahead of YC from former YC president Sam Altman, who recently stepped down from the role to focus on OpenAI, an AI research organization. Altman is said to have encouraged ZeroDown to complete the respected Silicon Valley accelerator program, which, if nothing else, grants its companies a priceless network with which no other incubator or accelerator can compete.

Overview .AI’s founders’ resumes are impressive, too. Russell Nibbelink and Christopher Van Dyke were previously engineers at Salesforce and Tesla, respectively. An industrial automation startup, Overview is developing a smart camera capable of learning a machine’s routine to detect deviations, crashes or anomalies. TechCrunch hasn’t been able to get in touch with Overview’s team or pinpoint the size of its seed round, though sources confirm it skipped Demo Day because of a deal.
Catch, for its part, closed a $5.1 million seed round co-led by Khosla Ventures, NYCA Partners and Steve Jang prior to Demo Day. Instead of pitching their health insurance platform at the big event, Catch published a blog post announcing its first feature, The Catch Health Explorer.
“This is only the first glimpse of what we’re building this year,” Catch wrote in the blog post. “In a few months, we’ll be bringing end-to-end health insurance enrollment for individual plans into Catch to provide the best health insurance enrollment experience in the country.”
TechCrunch has more details on the healthtech startup’s funding, which included participation from Kleiner Perkins, the Urban Innovation Fund and the Graduate Fund.
Four more startups, Truora, Middesk, Glide and FlockJay had deals in the final stages when they walked onto the Demo Day stage, deciding to make their pitches rather than skip the big finale. Sources tell TechCrunch that renowned venture capital firm Accel invested in both Truora and Middesk, among other YC W19 graduates. Truora offers fast, reliable and affordable background checks for the Latin America market, while Middesk does due diligence for businesses to help them conduct risk and compliance assessments on customers.
Finally, Glide, which allows users to quickly and easily create well-designed mobile apps from Google Sheets pages, landed support from First Round Capital, and FlockJay, the operator an online sales academy that teaches job seekers from underrepresented backgrounds the skills and training they need to pursue a career in tech sales, secured investment from Lightspeed Venture Partners, according to sources familiar with the deal.

Raising ahead of Demo Day isn’t a new phenomenon. Companies, thanks to the invaluable YC network, increase their chances at raising, as well as their valuation, the moment they enroll in the accelerator. They can begin chatting with VCs when they see fit, and they’re encouraged to mingle with YC alumni, a process that can result in pre-Demo Day acquisitions.
This year, Elph, a blockchain infrastructure startup, was bought by Brex, a buzzworthy fintech unicorn that itself graduated from YC only two years ago. The deal closed just one week before Demo Day. Brex’s head of engineering, Cosmin Nicolaescu, tells TechCrunch the Elph five-person team — including co-founders Ritik Malhotra and Tanooj Luthra, who previously founded the Box-acquired startup Steem — were being eyed by several larger companies as Brex negotiated the deal.
“For me, it was important to get them before batch day because that opens the floodgates,” Nicolaescu told TechCrunch. “The reason why I really liked them is they are very entrepreneurial, which aligns with what we want to do. Each of our products is really like its own business.”
Of course, Brex offers a credit card for startups and has no plans to dabble with blockchain or cryptocurrency. The Elph team, rather, will bring their infrastructure security know-how to Brex, helping the $1.1 billion company build its next product, a credit card for large enterprises. Brex declined to disclose the terms of its acquisition.
Y Combinator partners Michael Seibel and Dalton Caldwell, and moderator Josh Constine, speak onstage during TechCrunch Disrupt SF 2018. (Photo by Kimberly White/Getty Images)
Ultimately, it’s up to startups to determine the cost at which they’ll give up equity. YC companies raise capital under the SAFE model, or a simple agreement for future equity, a form of fundraising invented by YC. Basically, an investor makes a cash investment in a YC startup, then receives company stock at a later date, typically upon a Series A or post-seed deal. YC made the switch from investing in startups on a pre-money safe basis to a post-money safe in 2018 to make cap table math easier for founders.
Michael Seibel, the chief executive officer of YC, says the accelerator works with each startup to develop a personalized fundraising plan. The businesses that raise at valuations north of $10 million, he explained, do so because of high demand.
“Each company decides on the amount of money they want to raise, the valuation they want to raise at, and when they want to start fundraising,” Seibel told TechCrunch via email. “YC is only an advisor and does not dictate how our companies operate. The vast majority of companies complete fundraising in the 1 to 2 months after Demo Day. According to our data, there is little correlation between the companies who are most in demand on Demo Day and ones who go on to become extremely successful. Our advice to founders is not to over optimize the fundraising process.”
Though Seibel says the majority raise in the months following Demo Day, it seems the very best investors know to be proactive about reviewing and investing in the batch before the big event.
Khosla Ventures, like other top VC firms, meets with YC companies as early as possible, partner Kristina Simmons tells TechCrunch, even scheduling interviews with companies in the period between when a startup is accepted to YC to before they actually begin the program. Another Khosla partner, Evan Moore, echoed Seibel’s statement, claiming there isn’t a correlation between the future unicorns and those that raise capital ahead of Demo Day. Moore is a co-founder of DoorDash, a YC graduate now worth $7.1 billion. DoorDash closed its first round of capital in the weeks following Demo Day.
“I think a lot of the activity before demo day is driven by investor FOMO,” Moore wrote in an email to TechCrunch. “I’ve had investors ask me how to get into a company without even knowing what the company does! I mostly see this as a side effect of a good thing: YC has helped tip the scale toward founders by creating an environment where investors compete. This dynamic isn’t what many investors are used to, so every batch some complain about valuations and how easy the founders have it, but making it easier for ambitious entrepreneurs to get funding and pursue their vision is a good thing for the economy.”
This year, given the number of recent changes at YC — namely the size of its latest batch — there was added pressure on the accelerator to showcase its best group yet. And while some did tell TechCrunch they were especially impressed with the lineup, others indeed expressed frustration with valuations.
Many YC startups are fundraising at valuations at or higher than $10 million. For context, that’s actually perfectly in line with the median seed-stage valuation in 2018. According to PitchBook, U.S. startups raised seed rounds at a median post-valuation of $10 million last year; so far this year, companies are raising seed rounds at a slightly higher post-valuation of $11 million. With that said, many of the startups in YC’s cohorts are not as mature as the average seed-stage company. Per PitchBook, a company can be several years of age before it secures its seed round.
I did not talk to a single company in this batch raising under $10M post (admittedly I only was able to speak with a fraction of the 205).
— Peter Rojas (@peterrojas) March 20, 2019
Nonetheless, pricey deals can come as a disappointment to the seed investors who find themselves at YC every year but because their reputations aren’t as lofty as say, Accel, aren’t able to book pre-Demo Day meetings with YC’s top of class.
The question is who is Y Combinator serving? And the answer is founders, not investors. YC is under no obligation to serve up deals of a certain valuation nor is it responsible for which investors gain access to its best companies at what time. After all, startups are raking in larger and larger rounds, earlier in their lifespans; shouldn’t YC, a microcosm for the Silicon Valley startup ecosystem, advise their startups to charge the best investors the going rate?
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One of the hottest Y Combinator startups just raised a big seed round to clean up the mess created by Uber, Postmates and the gig economy. Catch sells health insurance, retirement savings plans and tax withholding directly to freelancers, contractors, or anyone uncovered. By building and curating simplified benefits services, Catch can offer a safety net for the future of work.
“In order to stay competitive as a society, we need to address inequality and volatility. We think Catch is the first step to offering alternatives to the mandate that benefits can only come from an employer or the government,” writes Catch co-founder and COO Kristen Tyrrell. Her co-founder and CEO Andrew Ambrosino, a former Kleiner Perkins design fellow, stumbled onto the problem as he struggled to juggle all the paperwork and programs companies typically hire an HR manager to handle. “Setting up a benefits plan was a pain. You had to become an expert in the space, and even once you were, executing and getting the stuff you needed was pretty difficult.” Catch does all this annoying but essential work for you.
Now Catch is getting its first press after piloting its product with tens of thousands of users. TechCrunch caught wind of its highly competitive seed round closing, and Catch confirms it has raised $5.1 million at a $20.5 million post-money valuation co-led by Khosla Ventures, Kindred Ventures, and NYCA Partners. This follow-up to its $1 million pre-seed will fuel its expansion into full heath insurance enrollment, life insurance and more. Catch is part of a growing trend that sees the best Y Combinator startup fully funded before Demo Day even arrives.

“Benefits, as a system built and provided by employers, created the mid-century middle class. In the post-war economic boom, companies offering benefits in the form of health insurance and pensions enabled familial stability that led to expansive growth and prosperity,” recalls Tyrrell, who was formerly the director of product at student debt repayment benefits startup FutureFuel.io. “Emboldened by private-sector growth (and apparent self-sufficiency), the 1970s and 80s saw a massive shift in financial risk management from the government to employers. The public safety net contracted in favor of privatized solutions. As technological advances progressed, employers and employees continued to redefine what work looked like. The bureaucratic and inflexible benefits system was unable to keep up. The private safety net crumbled.”
That problem has ballooned in recent years with the advent of the on-demand economy, where millions become Uber drivers, Instacart shoppers, DoorDash deliverers and TaskRabbits. Meanwhile, the destigmatization of remote work and digital nomadism has turned more people into permanent freelancers and contractors, or full-time employees without benefits. “A new class of worker emerged: one with volatile, complex income streams and limited access to second-order financial products like automated savings, individual retirement plans, and independent health insurance. We entered the new millennium with rot under the surface of new opportunity from the proliferation of the internet,” Tyrrell declares. “The last 15 years are borrowed time for the unconventional proletariat. It is time to come to terms and design a safety net that is personal, portable, modern and flexible. That’s why we built Catch.”
Catch co-founders Andrew Ambrosino and Kristen Tyrrell
Currently Catch offers the following services, each with their own way of earning the startup revenue:
These and the rest of Catch’s services are curated through its Guide. You answer a few questions about which benefits you have and need, connect your bank account, choose which programs you want and get push notifications whenever Catch needs your decisions or approvals. It’s designed to minimize busy work so if you have a child, you can add them to all your programs with a click instead of slogging through reconfiguring them all one at a time. That simplicity has ignited explosive growth for Catch, with the balances it holds for tax withholding, time off and retirement balances up 300 percent in each of the last three months.
In 2019 it plans to add Catch-branded student loan refinancing, vision and dental enrollment plus payments via existing providers, life insurance through a partner such as Ladder or Ethos and full health insurance enrollment plus subsidies and premium payments via existing insurance companies like Blue Shield and Oscar. And in 2020 it’s hoping to build out its own blended retirement savings solution and income-smoothing tools.
If any of this sounds boring, that’s kind of the point. Instead of sorting through this mind-numbing stuff unassisted, Catch holds your hand. Its benefits Guide is available on the web today and it’s beta testing iOS and Android apps that will launch soon. Catch is focused on direct-to-consumer sales because “We’ve seen too many startups waste time on channels/partnerships before they know people truly want their product and get lost along the way,” Tyrrell writes. Eventually it wants to set up integrations directly into where users get paid.
Catch’s biggest competition is people haphazardly managing benefits with Excel spreadsheets and a mishmash of healthcare.gov and solutions for specific programs. Twenty-one percent of Americans have saved $0 for retirement, which you could see as either a challenge to scaling Catch or a massive greenfield opportunity. Track.tax, one of its direct competitors, charges a subscription price that has driven users to Catch. And automated advisors like Betterment and Wealthfront accounts don’t work so well for gig workers with lots of income volatility.
So do the founders think the gig economy, with its suppression of benefits, helps or hinders our species? “We believe the story is complex, but overall, the existing state of the gig economy is hurting society. Without better systems to provide support for freelance/contract workers, we are making people more precarious and less likely to succeed financially.”

When I ask what keeps the founders up at night, Tyrrell admits “The safety net is not built for individuals. It’s built to be distributed through HR departments and employers. We are very worried that the products we offer aren’t on equal footing with group/company products.” For example, there’s a $6,000/year IRA limit for individuals while the corporate equivalent 401k limit is $19,000, and health insurance is much cheaper for groups than individuals.
To surmount those humps, Catch assembled a huge list of angel investors who’ve built a range of financial services, including NerdWallet founder Jake Gibson, Earnest founders Louis Beryl and Ben Hutchinson, ANDCO (acquired by Fiverr) founder Leif Abraham, Totem founder Neal Khosla, Commuter Club founder Petko Plachkov, Playable (acquired by Stripe) founder Tad Milbourn and Synapse founder Bruno Faviero. It also brought on a wide range of venture funds to open doors for it. Those include Urban Innovation Fund, Kleiner Perkins, Y Combinator, Tempo Ventures, Prehype, Loup Ventures, Indicator Ventures, Ground Up Ventures and Graduate Fund.
Hopefully the fact that there are three lead investors and so many more in the round won’t mean that none feel truly accountable to oversee the company. With 80 million Americans lacking employer-sponsored benefits and 27 million without health insurance and median job tenure down to 2.8 years for people ages 25 to 34 leading to more gaps between jobs, our workforce is vulnerable. Catch can’t operate like a traditional software startup with leniency for screw-ups. If it can move cautiously and fix things, it could earn labor’s trust and become a fundamental piece of the welfare stack.
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One way to gain ground on a competitor is to poach their best executives. We’ve seen it time and time again, from high-level Tesla employees fleeing for Lyft or Apple stealing Google’s AI talent.
DoorDash, a well-funded food delivery unicorn, is familiar with this method of staffing. The company announced this morning that it has poached its second Uber employee in the last year to join its growing business. Ryan Sokol, credited with leading and scaling Uber Eats, Uber’s food delivery arm, from its inception, has joined DoorDash as its vice president of engineering.
The news comes shortly after the San Francisco-based company hired Prabir Adarkar, Uber’s former head of strategic finance, as its chief financial officer. The company also recently hired chief people officer Sarah Wagener from Pandora, where she was VP of human resources.
Reporting to co-founder and chief executive officer Tony Xu, Sokol will lead the product, infrastructure and data science teams within DoorDash’s engineering department.
“Ryan comes to DoorDash at a critical inflection point in our business following a breakout year,” DoorDash wrote in an announcement. “In 2018 we 5xed our geographic footprint from 600 to 3,300 cities and tripled our valuation to more than $4 billion.”
“We doubled the engineering team to 200+ last year, working on a variety of problems from machine learning applications to logistics to personalizing consumer experiences,” DoorDash added. “This year, we plan to double our team again and continue on our trajectory as the fastest growing last-mile logistics company in the space.”
Six-year-old DoorDash has raised nearly $1 billion in venture capital funding, most recently at a $4 billion valuation, from SoftBank, Sequoia, Coatue Management, DST Global, Kleiner Perkins, Khosla Ventures, CRV and several others.
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A slew of venture capitalists known for high-profile exits — Kirsten Green of Forerunner Ventures, Keith Rabois of Khosla Ventures, Alfred Lin of Sequoia Capital and Alex Taussig of Lightspeed Venture Partners — have invested in Faire (formerly known as Indigo Fair), a 2-year-old wholesale marketplace for artisanal products.
A quick glance at Faire suggests it’s a combination of Pinterest and Etsy, complete with trendy, pastel stationery, soap, baby products and more, all made by independent artisans and sold to retailers. Faire has today announced a $100 million fundraise across two financing rounds: a $40 million Series B led by Taussig at Lightspeed and a $60 million Series C led by Y Combinator’s Continuity fund. New investors Founders Fund, the venture firm founded by Peter Thiel, and DST Global also participated. The business has previously brought in a total of $16 million.
The latest financing values Faire at $535 million, according to a source familiar with the deal.
If you’re feeling a little bit of déjà vu, that’s because a similar startup also raised a sizeable round of venture capital funding, announced today. That’s Minted . The 10-year-old company, best known for its wide assortment of wedding invitations and stationery, raised $208 million led by Permira, with participation from T. Rowe Price. Though Minted is first and foremost a consumer-facing marketplace, it plans to double down on its wholesale business with its latest infusion of capital, setting it up to be among Faire’s biggest competitors.
Like Minted, Faire leverages artificial intelligence and predictive analytics to forecast which products will fly off its virtual shelves in order to to source and manage inventory as efficiently as possible. The approach appears to be working; Faire says it has 15,000 retailers actively purchasing from its platform, including Walgreens, Walmart, Sephora and Nordstrom — a 3,140 percent year-over-year increase. It’s completed 2,000 orders to date, garnering $100 million in run rate sales, and has expanded its community of artists 445 percent YoY, to 2,000.
The company, headquartered in San Francisco, with offices in Ontario and Waterloo, was founded by three former Square employees: chief executive officer Max Rhodes, who was product manager on a variety of strategic initiatives, including Square Capital and Square Cash; chief information officer Daniele Perito, who led risk and security for Square Cash; and chief technology officer Marcelo Cortes, a former engineering lead for Square Cash.
“Our mission at Faire is to empower entrepreneurs to chase their dreams,” Rhodes wrote in a blog post this morning. “We believe entrepreneurship is a calling. Starting a business provides a level of autonomy and fulfillment that’s become difficult to find for many elsewhere in the economy. With this in mind, we built Faire to help entrepreneurs on both sides of our marketplace succeed.”
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