Welcome to spooky season in startups •

Welcome to Startups Weekly, a fresh human-first take on this week’s startup news and trends. To get this in your inbox, subscribe here.

A multibillion dollar acquisition, IPO projections and some good ol’ VC and billionaire drama?

It would be unfair to say that this week in tech and startups felt like 2021’s boom cycle; especially when you look at layoffs coming from Truepill, its fourth this year, and Meta announcing that it will freeze hiring. At the same time, it does feel like there’s a new feeling in the air. Heck, NFT marketplaces are still raising money. 

The market is not dull, but it’s not loud; and the mood among my sources is certainly closer to spooky than it is to savage. Besides the fact that, yes, I did grow up writing poetry about fall foliage before deciding that I wanted to be a journalist, I’m saying all this to validate the nuance of this moment.

The ideas that I’m looking toward throughout the end of the year are as follows:

• What happened to the black swan memos? In the early innings of the economic downturn, investors turned to portfolio companies to warn of an increasingly volatile environment. That conversation hasn’t disappeared, but it has certainly gotten quieter, with many investors now telling me that there’s a super surge of financing on the way. So, what’s the new guidance that is being sent to portfolio companies?
• What’s the human side of the layoff story? My colleagues Mary Ann and Christine gave us all an important lesson this week, which is that stories about workforce reductions should not revolve around the employer. The duo wrote about the human cost of Better.com’s layoff spree — full story here — and I’m not-so-subtly going to steal this idea. I want to talk to people impacted by tech’s 2022 layoff wave and hear what next steps look like. I hear it’s a lot more complicated than “you should’ve known your company was overhyped to begin with.”
• Finally, what are startups preparing to actually do differently? I’m guilty of this, but we often speak about startups and tech with generalizations, slightly hedged by explaining that it’s useful for directional purposes. I want to know what startups learned this year and are tactically doing differently. Spending with more discipline or focusing on the product doesn’t count; give me specifics, and better yet, tell me what you are disagreeing with your investors on.

Do let me know what yours are by tweeting at me or responding to this post. If you missed last week’s newsletter, read it here: “Tiger Global, fickle checks and the difficulty of acceleration.” We also recorded a companion podcast, here: “Building startups in public has an end date.”

In today’s newsletter, we’ll talk about the beauty of pivots, a creative way to prove that your startup hires entrepreneurial people and the latest from 500 global.

If you like this newsletter, do me a quick favor? Forward it to a friend, share it on Twitter and tag me so I can thank you for reading myself!

A reminder that pivots work

TC’s Rebecca Szkutak wrote about how a pivot helped HopSkipDrive win a difficult pitch to parents: Trust your kids with our ride-sharing services.

Here’s why it’s important: As we discussed in our latest Equity podcast, sometimes we’re all just a Hop, Skip and a Drive away from success. The “Uber for X” model has been MIA for a few years now, so the story behind HopSkipDrive and its trusty partner stands out to me. Who said schools weren’t experimental!

A different version of CVC, I guess

News broke this week that Cloudflare gathered $1.25 billion in financing for startups that use its own platform. Well, kind of.

Here’s why it’s important: The security, performance and reliability company didn’t raise a corporate venture fund, typical of other companies looking to breed entrepreneur attention. Instead, Cloudflare just got dozens of venture firms to offer to invest up to $1.25 billion to companies in their existing funds. It’s a little softer than a traditional investment vehicle, given that we don’t know how formal those offers of support are, and the fact that Cloudflare is not providing any funding or making any funding decisions.

To me, the commitment just tells us that Cloudflare wants to show startups that it doesn’t just make sense to use their software, it makes cents.

The follow-up

I’m experimenting with a new section in Startups Weekly, where each week we follow up with an old story or trend to see what’s changed since our first look. This week, we’re following up on our conversation about accelerator and demo days with a look at how 500 Global, formerly 500 Startups, thinks about it.

Here’s what’s new: It’s been a little over a year since accelerator 500 Startups rebranded to 500 Global in an attempt to reposition itself as a venture firm. In my latest for +, I spoke to Clayton Bryan, partner and head of 500 Global’s accelerator program, about how they keep up with competition. Excerpt down below!

The investor highlighted the effectiveness of rolling admissions, which its two main accelerator competitors, Y Combinator and Techstars, don’t do. Three years ago, 500 Global said it would decide on investments all year instead of just twice yearly. Demo days will still happen biannually, but startups can choose which demo day they want to be a part of.

“That change has really resonated with founders,” Bryan said. He compared the previous version of 500 Global to a school with an annual schedule: There are times when you’re doing homework, times when you sit back and recruit, and summer vacation. Now, it’s year-round, and he admits it’s more challenging to manage, “but at the same time, much more appreciated by the founders.”

“I do think it makes us more competitive,” he said. “We can more frequently talk to founders and they can start our program at different points in time. They don’t have to wait for that application to open or that deadline. Whereas [with] some other programs, they might say, ‘Hey, wait for a couple more months so we’re accepting applications again.’ I think that openness and flexibility gives us a bit of an advantage.”

A few notes

We’re less than one month away from Disrupt, and I’m already emotional. It’s going to be a blast, a pep talk, a realization and a week not to miss. Here’s the full agenda, and here’s where you can get your tickets.

While I have you, let’s talk some more. As you know, I co-host Equity, which goes out thrice a week and is TC’s longest-running podcast. We have some besties to listen to, too, including our crypto-focused show that goes by Chain Reaction and founder-focused show that goes by Found. The Podcast is also a can’t miss, so pay attention to all the good shows that they’re putting out. 

Seen on

Here are some of the cringiest revelations in the Elon Musk text dump

Why build a fintech any more when you can just raise €20M and white-label it to banks?

Instagram permanently disabled Pornhub’s account

EV charging deals keep coming, Ford squeezed by shortages and Kitty Hawk shuts down

Crypto platform Nexo sued by New York, California and six other US regulators 

Seen on +

Treepz founder Onyeka Akumah on how to succeed in transportation tech

What can the 2000 dot-com crash teach us about the 2022 tech downturn? 

Europe’s inaugural Women in VC Summit is the first step in a long climb toward equity

Venture investors hit the brakes on productivity software

Same time, same web page, next week?

N