Welcome to Startups Weekly, a fresh look at this week’s startup news and trends. To get this in your inbox, subscribe here.
It’s been a week of people trying to figure out what’s going on in tech. If you split: Cheers! Now let me tell you what happens.
On Monday, WeWork founder Adam Neumann raised a seed round from Andreessen Horowitz for a new real estate company, reportedly valued at more than $1 billion. Neumann’s return, along with the largest check ever written by one of the most famous firms, was met with with a set of reactions given his tumultuous leadership at WeWork.
One common response was that women and people of color will never get the same “second chance” as Neumann, because first chances are hard enough for a historically overlooked cohort. Alison Byers, the founder of Scroobious, a platform that aims to diversify startups and make founders more risk-averse, described the feeling as “muted anger.”
A few days earlier, Kimberly Bryant was fired from the nonprofit she founded, Black Girls Code, by the board she appointed.
You’re Caught Up: We had a comeback and an eviction that happened in the same week.
The return came from the white man who misled investors and employees. The one removed was a black woman who founded a non-profit organization to bring more diversity to the coding world.
If the analysis stops there, it is a disservice. As my colleague Dominique-Madori Davies said, “people talk about these things without the nuance of two things at the same time, but that’s also the case with most arguments online. They turn things and people into one-dimensional objects, as if this is easy to analyze. If you’re not careful, you can slip into an opinion that misses the multifaceted nature of the controversy.
Increasing the difficulty of growing as a diverse founder can end up building a pressure cooker that those who do land a check are forced to act. The pressure can make it harder for those same founders to make even one mistake.
For my full take, read my TechCrunch+ article: “Adam Neumann, Kimberly Bryant, and the Importance of Shade.” You can also listen to my latest podcast, “Let’s officially stop comparing Adam Neumann and Elizabeth Holmes.”
In the rest of this newsletter, we’ll look at Stripe’s scaling since the acquisition it made last year and the latest in the world of employee benefits.
As always, you can support me by forwarding this newsletter to a friend or follow me on twitter
The strip shrinks back
Stripe has fired some of the employees who support TaxJar, a tax compliance startup it acquired last year, TechCrunch has learned from multiple sources and first-hand documentation. TechCrunch contacted Stripe for confirmation, and a spokesperson said the company declined to comment.
According to LinkedIn, TaxJar co-founder Matt Anderson left Stripe in July, followed by people in the sales, marketing and partnerships teams.
Here’s why it’s important: Stripe bought TaxJar, a provider of a cloud-based suite of tax services, in April 2021 to help its customers “automatically calculate, report and file sales taxes.” At the time, Stripe told TechCrunch that all 200 employees of the Massachusetts-based business were joining the company. The purpose of the acquisition was to integrate sales tax collection and remittance as a service, one of the most requested features among users.
The winding down of go-to-market efforts for TaxJar customers began in late July, indicating a shift in Stripe’s outlook.

Image Credits: Miguel Candela/SOPA Images/LightRocket/Getty Images
Will your company cut your benefits or your co-workers first?
This week on Equity, I was joined by TC’s Rebecca Skutak to talk about everything from international money transfers to innovations in hearing aids. One conversation that stood out in the episode was the one about employee benefits.
Here’s why it’s important: Companies are rethinking their budgets, and the changes may come at the cost of more than your free Sweetgreen. In a TechCrunch+ analysis, Szkutak explores how startups can cope with employee benefits amid layoffs and a tight labor market. One source told her that “if a company has already lost a significant amount of employees because of the Great Resignation, a reduction in compensation can only add fuel to the fire.”
Me, it is particularly interesting to see that the B2B2C model is becoming less sticky. It used to be the place for any consumer-focused company to find a more reliable user base. After all, it was easier to sign an employer with thousands of clients, then to sign each of those clients independently. Since this pattern is threatened, some natural selection will definitely occur.

Image Credits: Bryce Durbin / TechCrunch
If you missed last week’s newsletter
Read it here: You’re not that special (there’s a starting angle here, I swear)
- Listen to TechCrunch’s other podcasts, including our crypto-focused show coming out of Chain Reaction and the founder-focused show coming out of Found. The TechCrunch podcast also continues to entertain me, so pay attention to all the good shows they put on.
- Remember, TechCrunch Live is on a brand new platform, and we’ve made it easier to apply for a pitch internship. Investors (and my inbox) can attest to the importance of brevity, comprehensibility and clarity in pitches, so it’s great to see. Startups can now apply any day and any time for Pitch Practice from filling out this form.
- Go mining for an opportunity in TC Sessions: Crypto, this November in Miami. Yes, you heard that right, we’re coming to Miami.
- finally TechCrunch Live is coming to Minneapolis. On September 7th, join the TechCrunch team as we interview the best and brightest in town. Minneapolis is among the best cities in the Midwest to start a company — and you’ll soon find out why!
Seen on TechCrunch
VSC Ventures adds $14 million to its storytelling and checkbook investment
The Three Real Results of a Robotic Startup
Your startup needs someone to be its lead storyteller
Wayfair will cut 5% of its workforce, or nearly 900 employees
Seen on TechCrunch+
5 Investors Explain Why Longevity Tech Is a Long-Term Play
Why do startup valuations fall when interest rates rise?
Pitch Deck Teardown: Mi Terro’s $1.5M Seed Deck
There’s a reason Midwestern startups have had fewer layoffs, says Chicago VC
Dear Sophie: How can I get an O-1 visa to freelance on web3 projects?
Ok, that’s all from me. I appreciate you endlessly!