Why Box is one of the most underappreciated companies – gpgmail


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

This week, we recorded on location at gpgmail Sessions: Enterprise in San Francisco, a show that saw talks from Box’s Aaron Levie, Atlassian CEO Scott Farquhar and venture capitalists Maha Ibrahim, Rebecca Lynn and Jason Green. The latter, the founder of Emergence Capital, joined us before his panel for a special episode of Equity focused almost entirely on enterprise tech. Danny Crichton, the esteemed leader of gpgmail’s Extra Crunch, was on hand to co-lead the episode with Kate.

Before we jumped too deep into the enterprise pool, we had to review some news from one of the most-talked about companies. The co-working giant, legally known as The We Company, is said to have halved its IPO exceptions to a minuscule $20 billion! Ok that’s not really that small but compared to its most recent valuation of $47 billion, we’re a bit shocked.

Next, we ran through the IPO pipeline. Cloudflare is expected to go public next Friday. Datadog will come after that. WeWork is reportedly kicking off its roadshow next week, but given this week’s reports, that could be delayed.

After that, Green gave us his take on Box, the file sharing business in which he was an early investor in. If you haven’t heard, activist investor Starboard Value took a 7.5% stake in the business this week. Green explains what that means and what he think is next for the company. Levie, of course, spoke on stage at the enterprise event. In short, the executive said his goal is to continue building a sustainable business.

Finally, we dove into the latest trends in startups. Enterprise still isn’t sexy but it’s much sexier than it’s been in the past. Why? Because all the enterprise startups want to build consumer friendly tools. Tune in to hear what Green thinks of the consumerization of the enterprise and all the startup madness.

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


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The myth of “stage agnostic” investing – gpgmail


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

This week we were helmed by Kate Clark, Alex Wilhelm, and yet another extra special guest. Unusual Ventures co-founder and partner John Vironis joined us to talk soil investing (yes, it’s a thing), seed investing, growth investing and all the somewhat meaningless funding stages.

Vrionis was a longtime investor at Lightspeed Venture Partners and has made big bets on a number of companies, including AppDynamics, Heptio, and Mulesoft.

It was a great episode that kicked off with some conversation around DoorDash, the food delivery company that continues to make headlines week after week. We’d like to stop talking about the company, but it intrudes regularly into our notes.

This time DoorDash bought a few companies, purchases that appear set to allow the firm to boost its investment and research into self-driving delivery robots. (Kate saw one in the wild recently!)

Next we went deep into the subject of seed. John, of course, has been a seed investor for years and has lots to say on the topic. Mostly, we discussed Kate’s latest piece on mega-funds making an increasing number of deals at the earliest stage. John doesn’t think “stage-agnostic” investing makes any sense. You need experts at each stage making bets on a specific type of company. In his words, ‘a heart surgeon wouldn’t deliver your baby, right.”

Then we moved onto one of our favorite subjects, namely direct listings, the IPO market, and if money is too often left on the table. The question takes on extra import when we see results like Dynatrace’s IPO, which rose around 50 percent its first day. It seems likely that we’ll see other companies pursue the sort of direct listings that Spotify and Slack managed.

That segued us brilliantly into our final topic: Airbnb and its financial health. The firm, we reckon, is a good candidate for a direct listing itself. We talked over its numbers, and if we were to sum our perspectives, we’d say that Airbnb is about as impressive as we expected.

All that and we had fun, as usual.

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




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Watch YC CEO Michael Seibel chat startups, prices, and tech’s center of gravity – gpgmail


This week, nearly 200 startups convened at Y Combinator Demo Day to pitch venture capitalists, angels and other folks looking to spend some money.

YC chief executive officer Michael Seibel took some time out of his busy schedule to join us on a special episode of Equity, gpgmail’s venture-capital-focused podcast. Given that we had Seibel to chat with, Kate and Alex decided to drop the regular format and riff interview-style about what the accelerator program is up to.

We discussed the new startup batch (roundups here, here, and here), recent changes to the program, rising deal prices, SAFEs versus convertible notes and the future of technology in San Francisco. Regarding price, here’s what Seibel had to say:

“It’s a competitive market where investors are bidding against each other. So if you see pricing go up you have to ask yourself the question, ‘where is the money supply coming from?’ The big trend over the last six years has been institutional investors moving from just kind of Series A funds and growth funds down to the seed level. When you looked at Demo Day when I was going through the first time it was full of angels – people investing off their own personal balance sheet. And if you look at the room today it’s full of funds. The reality is that, as the pool of capital increases in the seed world, the seed investors are competing against each other and one of the easier ways for investors to compete is to bid up price.”

But, Seibel continued, YC doesn’t necessarily consider the situation a net-positive, because companies that raise such huge rounds can spend money as though they had reached the fabled “product-market fit,” when in reality they have not. They just have money, which can feel the same but is not.

Ultimately, the thing that’s going to kill you, Seibel says, isn’t fundraising or who you raised from. The thing that’s going to kill you, he says, is that you didn’t build something your customers wanted.

Watch a clip from the interview here:

To hear more from Seibel and watch four more video clips discussing YC, the new class, and the startup game in San Francisco and beyond, become an Extra Crunch member. You can learn more and try it for free. 




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Making sense of the WeWork S-1 (or trying to) – gpgmail


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

Today is our promised Equity Shot (a short-form, single-topic episode) on the WeWork S-1. You can read Kate’s notes here, or Alex’s here as a place to start.

Given that we didn’t know when the WeWork S-1 filing was going to make itself known, we put together this episode from gpgmail’s SF HQ, Alex’s home office, and Kate inside a New York Blue Bottle Coffee. We were not about to let the locational issues stop us from having fun!

Where to begin! WeWork is growing like mad, but it’s hard to tell what its gross margins are. This makes its revenue quality hard to parse. (Alex tried to figure that out here, gpgmail has even more good questions and notes here). What wasn’t hard to figure out was that WeWork — also known as The We Company — is tectonically unprofitable on operating and net bases. And that the company’s operations consume cash, while its investing activities torch the stuff.

WeWork’s eclectic chief executive officer and co-founder Adam Neumann will maintain a majority of voting rights. It’s not uncommon for founder-led companies to adopt this sort of voting structure and considering how central Neumann is to WeWork’s identity, we weren’t the least bit surprised by this.

The company’s IPO will make a lot of groups a lot of money. Mainly Benchmark, a respected venture capital fund, JP Morgan, and, of course, SoftBank, which has invested billions in WeWork and now owns more than 100 million shares.

And that’s all for now. Don’t miss our episode with Dan Primack that came out yesterday. A busy week, but a good one. Chat again soon!

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




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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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Startups seek sperm… And venture capital backing – gpgmail


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

This week we were helmed by Kate Clark and Alex Wilhelm, but those of you who love the show having guests on don’t despair. As we explain at the top, there’s a lot of folks coming on the show soon, many of whom you know by name.

But that’s to come, and we had a lot to chat through this week. Including, right from the jump, the latest gyrations in the stock market. Earlier this week tech stocks, and especially cloud and SaaS stocks, took a nosedive. Sentiment swung around later in the week when markets caught their breath and Lyft’s earnings went well. But the movement in highly-valued SaaS companies caught our eye. Perhaps if the market finally does correct, we’ll see growth stakes take the worst of it.

But it wasn’t all bad news on the show, a new app that raised $5 million caught Kate’s attention. It’s called Squad and it’s now backed by First Round Capital, the seed fund behind the likes of Uber . You can read Kate’s interview with the founder, Esther Crawford, here.

Next, we turned to two startups that are focused on male reproductive health. While we’ve covered startups focused on fertility before on the show, this is the first time we’ve delved into male-focused services that are designed to help men take part in conception. The news here is Dadi has raised another $5 million in venture capital funding. Legacy, the other male fertility company we discussed, is taking part in Y Combinator’s summer batch right now.

On the IPO-ish beat, we talked about Postmates which has a new stadium partnership, and, more importantly, permission to use cute robots to deliver things in San Francisco. After hearing about how small, rolling robots will handle last-mile deliveries for years, we’re excited for them to actually make it to market. In our view, technology of this sort won’t eliminate the need for human workers at on-demand shops, though they may replace some routine runs. Bring on the burrito robots.

We closed on Airbnb’s purchase of Urbandoor, yet another acquisition from the popular home-sharing company that will eventually go public. It has to, right? Perhaps Urbandoor will help unlock new revenues in the corporate travel space before we see an S-1. After all, Airbnb wants to debut with plenty of growth under its belt to help it meet valuation expectations. Adding revenue to its core business could be a good way to ensure that there’s new top-line to report.

More to come, including something special next week!

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




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