Y Combinator Demo Day, revenue-based VC funding, Pivotal, Dell, Tumblr, WeWork, and more – gpgmail


Editor’s note

Due to bad travel logistics (thanks SFO), I wasn’t able to get the mid-week edition of the Extra Crunch roundup newsletter out. Sorry about that. Instead, here is everything we published this week on Extra Crunch in one fell swoop — and my, we covered a lot of ground. Hope you enjoy some great weekend reading.

Y Combinator Demo Day Coverage-a-palooza

Much like the equinoxes that synchronize Earth’s calendar, Y Combinator’s biannual demo days are a key fixture of the Silicon Valley calendar. This year was no different, with 166 companies presenting from the summer batch (and occasionally from previous batches if they chose to delay their presentation).

We had a full squad on site not only covering the 84 companies from day one and 82 companies from day two, but our team also put their collective heads together to identify the top companies from each set exclusively for Extra Crunch members.

The 11 best startups from Y Combinator’s S19 Demo Day 1

Read our favorite 11 startups from day one, which included:

PopSQL provides collaborative SQL query editing. You can store SQL queries you run regularly, grouping them into folders that can be kept private or shared amongst your team. Version history tracks changes so it can be reverted if/when something breaks. It currently has more than 100 paying companies, and is making $13K per month. It plans to build a marketplace for apps that run on top of your company’s database.

Why it’s one of our favorites: SQL database queries can be a nightmare, especially if they’re not something you’re used to dealing with every day. PopSQL lets you hammer on queries collaboratively until they’re working exactly as you want — then you can save them for future use and share them amongst your team members. And when you’ve spent the last 45 minutes trying to figure out why your query isn’t working only for a team mate to fix it in thirty seconds, you can use version control to see exactly what they changed. PopSQL says its product has already found customers in companies like Instacart, Redfin, and DoorDash.

Our 12 favorite startups from Y Combinator’s S19 Demo Day 2

Read our favorite 12 startups from day two, which included:

Business Score is helping companies automate background checks on other businesses. The startup is looking to stamp out tired manual processes that largely mean picking up the phone and scouring documents. The single API taps data sources across the web to build out real-time profiles that can help customers scan businesses in an effort to prevent fraud, qualify leads and onboard new clients.

Why it’s one of our favorites: Though it’s yet another startup in the batch catering to other startups, we thought Business Score stood out. The company integrates with thousands of data providers to help companies verify other startups and enterprises they are considering doing business with, using a system they’ve dubbed “the business passport.” There’s an opportunity here to create a tool essential to company-building across industry.

YC is doubling down on these investment theses in its most recent batch

Finally, amidst all the zany craziness of watching 166 companies present over two days (there should be a YC company for unmelting your brain), our venture capital reporter Kate Clark stepped back to assess what all the various companies in the batch indicated about the accelerator’s strategy these days.

YC knows its sweet spot: enterprise SaaS. One might go as far as to say it’s transitioning into a full-on SaaS incubator. Why? Because one of the greatest advantages of going through YC is the network of alumni companies you can tap into. Many successful B2B companies have emerged from the program, raised boat loads of venture capital funding and rocketed to the moon (hello Stripe, Brex, Gusto and Atrium). With that in mind, YC is doubling down on its resources for startups that sell products to other startups, which brings us to our first piece of news.

YC chief executive officer Michael Seibel and president Geoff Ralston announced this week that the accelerator has implemented something called CTO and HR demo days. In short, CTO and HR demo days are an opportunity for B2B startups to pitch their products to YC alum companies’ CTO and/or head of HR. Seibel and Ralston said 60 CTOs attended the event, as well as 30 HR heads. In total, 42 startups presented and we’re guessing a bunch of those companies booked a few customers.


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Tumblr’s next step forward with Automattic CEO Matt Mullenweg – gpgmail


After months of rumors, Verizon finally sold off Tumblr for a reported $3 million — a fraction of what Yahoo paid for the once might blogging service back in 2013.

The media conglomerate (which also owns gpgmail) was clearly never quite sure what to do with the property after gobbling it up as part of its 2016 Yahoo acquisition. All parties has since come to the conclusion that Tumblr simply wasn’t a good fit under either the Verizon or Yahoo umbrella, amounting to a $1.1 billion mistake.

For Tumblr, however, the story may still have a happy ending. By all accounts, its new home at Automattic is far better fit. The service joins a portfolio that includes popular blogging service WordPress.com, spam filtering service Akismet and long-form storytelling platform, Longreads.

In an interview, this week, Automattic founder and CEO Matt Mullenweg discussed Tumblr’s history and the impact of the poorly received adult content restrictions. He also shed some light on where Tumblr goes from here, including a potential increased focused on multimedia such as podcasting.

Brian Heater: I’m curious how [your meetings with Tumblr staff] went. What’s the feeling on the team right now? What are the concerns? How are people feeling about the transition?


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Axios’ Dan Primack on ‘the most polarizing startup that exists’ – gpgmail


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

This week was a bit special. Instead of meeting up at the gpgmail HQ to record the episode, Kate and Alex met up in muggy Boston at Drift’s office, where we linked up with Axios’s Dan Primack. And since we were feeling chatty, we went a bit long.

After checking in with Primack (he has a newsletter and a podcast), we first dealt with the latest from Tumblr. In short, Verizon Media is selling Tumblr to Automattic for a few dollars. How did Verizon wind up owning Tumblr? Ah. Well, Yahoo bought it. Later, after Verizon bought AOL, it bought Yahoo. Then it smushed them together and called it Oath. Then Verizon decided that it didn’t like that much and renamed the group Verizon Media. But Verizon doesn’t want to own media (besides gpgmail, of course), so it sold Tumblr to Automattic, a venture-backed company best known for operating WordPress.

That’s a lot, I know. What matters is that Yahoo bought Tumblr for more than $1 billion. Verizon sold it for around $3 million. Now, Automattic now has a few hundred new employees and a shot at juicing its userbase before it goes public.

After that, we lamented that the WeWork S-1 had yet to appear. This was a tragedy, frankly. We had expected to spend half the show riffing on WeWork’s financials, alas…

So we turned to some normal material, like Ramp’s recent $7 million raise to take on Brex, and, SmartNews’s recent round, which gave it an eye-popping $1.1 billion valuation.

We ran a bit long because we were having fun, fitting in some conversation surrounding the notes from the SEC regarding the now-dead and then-fraudulent Rothenberg Ventures. More on that here if you want to get angry.

And finally, Vision Fund 2. It’s been a big source of interest for everyone on the show, and we expect whatever the second-act Vision Fund winds up becoming to be a big damn deal. The fund will invest in more than just consumer marketplaces, in fact, it’s eyeing more AI businesses and even biotech. That should be interesting.

All that and we have a lot more good stuff coming. Thanks for listening to the show, and we’ll be right back.

Equity drops every Friday at 6:00 am PT, so subscribe to us on Apple Podcasts, Overcast, Pocket Casts, Downcast and all the casts.




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