On the record about
3 people · 15 quotes · 23 Mar 2012 to 20 May 2026
1 of 3 lane rests on fewer than 5 quotes and is marked thin. Offsets are days from the middle first-quote date, 23 Jun 2020 — a date, and nothing else. It is not a claim about who reached a view first.
Gurley describes cloud-connected workflows from business to consumer through apps as unexploited white space across verticals.
“Once it's in the cloud, they connect to Zillow, they connect to rent.com, they push the listings out, they communicate with the end user of the apartment, and so this workflow that starts to be connected from the cloud to the small business, to the consumer, to the smartphone app, that's all white space in a bunch of different verticals.”
Gurley predicts the next ten years will involve removing enterprise technology and moving systems outside via SaaS.
“I say we spent forty years cramming technology into the enterprise. We're going to spend the next ten yanking it out. It's just so wholesale that you're moving systems outside.”
Gurley explains why targeting sales instead of HR made Salesforce wildly more successful than their HR SaaS company.
“the sales executive has a green light on any purchase in a company. The HR executive does not. They had a product where you could put it on a credit card.”
Gerstner argues AWS, GCP and Azure enable software companies to reach much higher IPO valuations than Salesforce did.
“Compare where the software companies that are in the pipeline or that have recently gone public, compare those valuations to where Salesforce went public.”
Gurley cites twelve-year bull run and extreme SaaS multiples as major IPO incentives.
“Add into that a roaring, screaming public market that's been on a bull run for, what, twelve years? And multiples in the public markets, especially in, the SaaS world that are out of this world.”
Gerstner cites Snowflake growing free cash flow over 100% annually with Q4 revenue of $1.4B versus $1.2B prior year.
“Snowflake this year will grow its free cash flow at over a 100% a year, next year probably, you know, 80 or 90%. Free cash flow, not just revenue, free cash flow.”
“And so what really values companies, you know, it's typically a discounted cash flows. And so now all of a sudden, the buy side's asking SaaS companies about net dollar retention, about long term operating margin, about whether their free cash flow is greater or less than their net income, about SBC as a percentage of free cash”
Gurley criticizes price-to-revenue multiples as the crudest possible valuation tool for evaluating companies.
“price to revenue is like this really crude valuation tool, it's like the crudest you could possibly have.”
Gurley lists specific new scrutiny metrics buyers now apply to SaaS companies beyond crude price-to-revenue multiples.
“what really values companies, you know, it's typically a discounted cash flows and so now all of a sudden the buy side's asking SaaS companies about net dollar retention, about long term operating margin, about whether their free cash flow is greater or less than their net income, about SBC as a percentage of free cash flow.”
Baker argues SaaS companies are repeating brick-and-mortar retailers' mistake by rejecting AI due to lower margins.
“Well, I think that application SaaS companies are making the exact same mistake that brick and mortar retailers did with e commerce.”
Baker argues SaaS companies are repeating brick-and-mortar retailers' mistake by rejecting lower-margin AI business.
“I think that application SaaS companies are making the exact same mistake that brick and mortar retailers did with e commerce.”
Baker notes AI companies generate cash earlier than SaaS despite lower margins due to fewer employees.
“The crazy thing is because of those efficiency gains, they're generating cash way earlier than SaaS companies did historically, but they're generating cash earlier, not because they have high gross margins, but because they have very few human employees.”
Baker says AI companies generate cash earlier than SaaS despite lower margins because they have very few human employees.
“And it's just tragic to watch all of these companies. Like you want to have an agent, It's never going to succeed.”
Baker says Anthropic added $11B ARR, comparing it to the entire SaaS revolution's $5-10T value creation.
“Anthropic, they added $11,000,000,000 of AR. And what is astonishing to me about this is that the SaaS and cloud revolution it created, we'll call it between 5 and $10,000,000,000,000 of value.”
Baker says Anthropic added $11B ARR in one month, matching what Palantir, Snowflake, and Databricks built in ten years combined.
“And these three companies employ thousands of people, tens of thousands collectively. They've all spent ten years building their businesses and Anthropic added their combined businesses in one month.”