Investors know when a founder is desperate. Sasha Orloff has raised a collective $1 billion in his career and he shares his advice for staying on top of your financial situation.

Listen to the full episode of Build Mode with Puzzle’s founder and CEO:

Stripe claims “the singularity” is here, and justifies its $7.5B acquisition of OpenRouter.

The truth, as the Equity podcast crew highlights, is much more practical, as unglamorous as token expense management may seem:

Andreessen Horowitz has two partners sitting on the boards of companies that now compete with each other: Ben Horowitz at Databricks and Martin Casado at Fivetran. Nothing too scandalous on the surface, except ⁠the Department of Justice has reportedly been investigating the arrangement ⁠for almost a year, dusting off a 112-year-old antitrust law that’s rarely used against VCs. 

Board conflicts aren’t exactly new, and these companies weren’t necessarily direct competitors when a16z first invested in them. But as portfolio companies expand into each other’s markets, the DOJ’s scrutiny raises a much bigger question for venture firms: How do you manage board seats when the boundaries between your portfolio companies keep moving? 
 
On this episode of TechCrunch’s⁠ Equity⁠ podcast, Kirsten Korosec, Anthony Ha, and Sean O’Kane dig into the a16z probe, what it could mean for VCs, and more of the week’s headlines. 

Subscribe to Equity on ⁠YouTube⁠,⁠ Apple Podcasts⁠,⁠ Overcast⁠,⁠ Spotify⁠ and all the casts. You also can follow Equity on⁠ X⁠ and⁠ Threads⁠, at @EquityPod. 
 
Chapters: 
 
00:00 Intro 
1:02 TechCrunch Disrupt and the Startup Battlefield 200 
3:17 The DOJ is investigating a16z over board seats 
14:47 Why Stripe just paid $7.5B for “the Stripe for AI” 
18:18 The mid-tier AI scramble: gateways, pivots, and acquihires 
23:17 Anthropic’s revenue surges while OpenAI’s losses deepen 
27:08 Also raises $150M and drops the “micro mobility” label 
32:30 Uber teams up with Zipline for drone delivery 
37:19 Wispr hits a $2B valuation 
38:26 Outro