Olive AI raised $850 million. Hit a $4 billion valuation. Signed up 900 hospitals. Backed by Tiger Global and General Catalyst. They were supposed to be the AI that finally fixed healthcare's biggest headache, the administrative chaos that costs the system billions every year.

Then they quietly sold off their assets and disappeared.

If you've ever wondered how a company with nearly a billion dollars and hundreds of customers can still manage to lose everything, this episode is your answer.

A quick breakdown of the SaaS deals, shifts, and signals that actually matter. Each week, we unpack the five most important moves in B2B tech, from who's buying what, to where the smart money is going, and give you two immediate audits to run on your own stack. No corporate jargon, just the insight you need to build, invest, or compete smarter.

A unicorn, a data hoard, and free AI employees on GitHub

Here's the Newsletter, if you prefer to read on the go: https://techstackbreakdown.substack.com/

Bench was supposed to be the future of small business bookkeeping. $100 million raised, 35,000 paying customers and backed by Shopify and Bain Capital. With real human bookkeepers, powered by slick software, all for a flat monthly fee. Entrepreneurs loved it.

Then, on December 27th, 2024 , Bench locked its doors. No warning, no data, just gone.

Whether you're a founder, an operator, or just someone who loves a good cautionary tale, there's something in here for you.

Hit play, learn from their mistakes, and build something that actually lasts.

A quick breakdown of the SaaS deals, shifts, and signals that actually matter. Each week, we unpack the five most important moves in B2B tech, from who's buying what, to where the smart money is going, and give you two immediate audits to run on your own stack. No corporate jargon, just the insight you need to build, invest, or compete smarter.

Salesforce kills the UI, an Italian rollup buys Miro, and Microsoft's biggest patch ever.

We unpack:

• Salesforce betting the keynote on killing the UI

• Salesforce's seven named AI agents (and what they mean for seat-based pricing)

• Bending Spoons acquiring Miro for $1.36B, the software rollup is real

• SAP's Patch Day: 19 vulnerabilities, one rated a perfect 10.0

• Microsoft's record-breaking Patch Tuesday: 974 vulnerabilities in one day

Here's the Newsletter, if you prefer to read on the go: https://techstackbreakdown.substack.com/

Jasper AI was the golden child of the AI boom. $125 million raised, a $1.5 billion valuation, and 70,000 paying customers. They had Super Bowl ads, Times Square billboards, and a product that marketers loved.

Then OpenAI dropped ChatGPT. For free. And Jasper... crumbled.

If you're building in AI, raising money, or just love a good tech tragedy, this one's for you!

Hit play, learn from their mistakes, and build something that actually lasts.

A quick breakdown of the SaaS deals, shifts, and signals that actually matter. Each week, we unpack the five most important moves in B2B tech, from who's buying what, to where the smart money is going, and give you two immediate audits to run on your own stack. No corporate jargon, just the insight you need to build, invest, or compete smarter.

Salesforce ditches the seat, Perfios wires up credit, and 91% of SaaS has a hidden flaw

Five stories about the old ways of measuring, pricing, and securing software, quietly falling apart.

We unpack:

- Salesforce moving from seats to outcomes

- Actionable predicting churn from operational data (not surveys)

- Perfios running India's lending backbone on autonomous agents

- India's IT giants redesigning work around AI

- Cyber Chief catching 91% of vulnerabilities that annual pen tests miss

Here's the Newsletter, if you prefer to read on the go: https://techstackbreakdown.substack.com/

InVision was the prototyping tool for designers. $350 million raised, $2 billion valuation and 7 million users with customers like Uber, Netflix, and Airbnb. They had it all, hype, funding, a product people loved.

Then Figma showed up. And InVision... vanished.

If you're building a product, raising money, or just love a good tech tragedy, this one's for you!

Hit play, learn from their mistakes and build something that lasts.

A quick breakdown of the SaaS deals, shifts, and signals that actually matter. Each week, we unpack the five most important moves in B2B tech, from who's buying what, to where the smart money is going, and give you two immediate audits to run on your own stack. No corporate jargon, just the insight you need to build, invest, or compete smarter.

Amazon buys a database team, Google kills your opt-out, and AI bills get a watchdog

Here's the Newsletter, if you prefer to read on the go: https://techstackbreakdown.substack.com/

How does a company with $120 million in funding, Stripe as a lead investor, and a product people actually use, just completely collapse?

In this episode of How They Killed It, we crack open the Fast autopsy.

If you're building a SaaS company, this one's for you. 

Hit play, learn from their mistakes and build something that lasts.

A quick breakdown of the SaaS deals, shifts, and signals that actually matter. Each week, we unpack the five most important moves in B2B tech, from who's buying what, to where the smart money is going, and give you two immediate audits to run on your own stack. No corporate jargon, just the insight you need to build, invest, or compete smarter.

A $43B buyout, a stake in dirt, and an elevator app that's actually smart

Here's the Newsletter, if you prefer to read on the go: https://techstackbreakdown.substack.com/