Episode 1: The Rise of Rippling

Top News

Rippling rising: TechCrunch reports that Rippling, the HRtech giant that manages quite a lot of global payroll, has raised a $450 million Series G round of funding that pushes its valuation to $16.8 billion — up from $13.4 billion last year. The company is in the midst of a high-visibility scrap with competitor Deel, after the latter company allegedly hired someone on the inside to exfiltrate its critical information. Rippling competes with Deel, Gusto, Remote, and several other companies that want to take on traditional HR tasks for companies that do not specialize in the work. One day, one of them will go public. But it is not this day.
Investing in Chinese AI is risky: Benchmark invested in Chinese AI company Manus, leading a $75 million round into the viral concern. Manus became best-known earlier this year for a demo of its agentic software that could complete complex tasks on behalf of users. Seeing a venture capital firm invest in potentially breakout technology is not surprising. But, with tensions between China and the United States running hot, the US Treasury Department is “reviewing” the deal, Semafor reports. Benchmark figured that as Manus isn’t building its own models, rules about AI investment wouldn’t apply. We’ll see..
AI rules are out of favor: In testimony before the Senate this week, leaders from OpenAI, CoreWeave, Microsoft, and AMD disbursed their views on AI, regulation, and competition. The gist? Regulation is now very much out of favor. As Alex notes, that’s a bit of a turnaround for OpenAI’s Sam Altman. But from the amoral business perspective, fighting for regulations when you are the undisputed market leader makes sense. And arguing against regulations when you have a host of capable competitors? Not so smart.

TWiST500

As promised, we have a host of new TWiST500 companies today. To avoid making you wait, here’s the list:

Some of the names on the list are companies that I have tracked for ages, startups like Monte Carlo, Alpaca, and Timescale. Some are very recently unveiled, like Slate.AUTO. And others are names that we’ve become more familiar with through news and, let’s be honest, research, like Sentra and Airbyte.

As always, we have another batch of names cooking. But as we get closer to 400, we’re not that far away from a full list. So, it’s going to get tricky on the selection front, and we might start cycling names on and off as needed. Call it a work in progress.

On the news front, Scale — which I would have bet you a car we had added ages ago — is likely now in the clear over alleged labor violations after the “U.S. Department of Labor has dropped its investigation into Scale AI’s compliance with the Fair Labor Standards Act,” TechCrunch reports. There’s been some debate about whether or not tech friends of the second Trump administration are getting their money’s worth. Here, in one case, the answer appears to be yes.

More Monday! — Alex

A message from LinkedIn Jobs

A business is only as strong as its people, and every hire matters. Go to https://www.linkedin.com/twist to post your first job for free. Terms and conditions apply.

This Week in Startups

E2123: On Friday’s TWiST, Jason, Alex and Lon debate why Instacart CEO Fidji Simo left that job to join the team at OpenAI: was it just the money, or a chance to do something more COMPELLING than helping people order groceries? Plus, everyone’s thoughts on the US justice system’s first-ever AI-generated victim statement, Jason urges viewers to read “The Checklist Manifesto,” and a chat with Where2Wheel founder Brittany Peregoff about her off-roading marketplace and the economic promise of agritourism.

E2122: It’s yet another overstuffed TWiST full of the tech news and founder insights you CRAVE. Jason, Alex, and Lon are talking about Zoox’s robotaxi recall (and why it’s not as bad as it sounds!), Coatue’s innovative new take on venture funds, NSO’s mega-fine for making spyware, and terrifying AI prophecies from the future. Plus Evan from FusionAds stops by to talk about automating marketing for your small business AND the Final Four of our Founder Friday tournament is now a FINAL FIVE!

E2121: On a Monday TWiST, Jason, Lon and Alex welcome Magical Toys chief Fateen Anam Raffid to talk about building next-generation AI toys and his company’s mega-growth ahead of the holiday season. PLUS the latest on Cursor’s explosive growth and massive $9B valuation, Uber’s latest autonomous vehicle partnerships, and Jason shares some anecdotes from F1 in Miami.

TWiST Partner Offers

Brex: Runway is everything for startups. That’s why 1 in 3 startups choose Brex for modern checking, treasury, and FDIC in one account. Learn more at https://www.brex.com/banking-solutions
Squarespace: Turn your idea into a new website! Go to https://www.Squarespace.com/TWIST for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.
Vanta: Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist

Want to Work for This Week in Startups?

We’re looking to fill two in-person sales positions at our Austin, Texas HQ! First, a high-performing Sales Executive to help us seek out and promote clients, sponsorships, branded content, and more. Plus an experienced Sales Manager to lead, coach, and scale our sales executive team, while setting performance goals. Love the podcast and have B2B sales experience? We want to hear from you!

SF Live-Work Space Now Available

Need a flexible living and working environment in San Francisco? This thoughtfully designed loft-style residence at 787 Bryant St., the heart of the vibrant SOMA district and the city’s creative hub, is now available for rent or purchase. Check the listing for more details.

Founder University

Applications are open for Founder University Cohort 11, a 12-week remote pre-accelerator program tailored towards navigating early-startup practices, building an MVP, and growing traction. Submit your application at Founder University— Cohort 10 will kick off Summer 2025!

LAUNCH Accelerator

Are you a pre-Series A founder with a product in the market? Applications are now open for LAUNCH Accelerator's 35th cohort—starting Summer 2025—where you'll perfect your pitch, grow your business, and connect with top Silicon Valley investors. Apply here and take your startup to the next level!

The TWiST500 newsletter is the new, updated, and improved TWiST Ticker.

Update your email preferences or unsubscribe here

548 Market Street PMB 72296
San Francisco, California 94104, United States of America