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The new CEO of Starbucks insisted on starting as a barista for 6 months He called together his inherited management team for an offsite None knew how to make an espresso

Today, Thiel, Sacks and Page prepare to leave California tomorrow. - Offices opened in Miami and Austin — today by Thiel - Driver’s Licenses Changed - Homes already owned California has approximately 255 billionaires — about a quarter of the U.S. total. The tax was estimated to raise $100B from ~200 of them. But as they scatter to Miami, Austin, and beyond, that number could shrink fast. It has already begun.

First time reporting to a CEO? 3 simple things to learn: - admit your mistakes. CEOs make even more of them. They get it. - end excuses. Those don't work anymore. - when you bring up a problem, make sure you also bring a solution. Do just this, you'll excel.

Spouse teams don't work - Eventbrite Solo founders don't work - Zoom Need to move to SF - Shopify Winner takes all - Marketo Remind me the other rules again

Tough lesson for CEOs to learn: You have to treat Great employees differently from Good ones Great ones want their careers enabled, want you to have their back, and want no politics. That's about it. Let them run. Good ones want many other, varied things. And need much more.

"Peter Thiel fired Elon Musk. Be -- he was kind about it. And he left Elon with all his economics (12% of PayPal). Be kind. He did what he had to do, but he was kind. And then Elon went back to Peter, and Founders Fund got to invest $20m to buy 10% of SpaceX. Perhaps the…

You think startups are about a great idea But in the end they are about being great at recruiting

To be a great CEO, You have to enjoy telling certain stories over and over again Sometimes 100s of times

My take on California’s “One-Time” Billionaire Tax. It’s much worse than it looks. 📉 Will it pass? Yes, likely. It only needs 50%+1 voter approval. SEIU + CTA have done this before—Prop 55 won 63% in 2016. ⚖️ Will it get tied up in litigation? Almost certainly. Retroactive wealth tax on a tax type CA has never had = due process challenges. Billionaires have the legal budgets for years of fights. 👋 But it’s clearly … only the start. The goal is an annual tax, not one-time. And the target is $25m-50m net worth folks, including illiquid foldings (early stage founders raising a Series B). The “one-time” framing is strategic, not terminal. The same coalition (CTA, CFT, SEIU) already has AB 259 written—an >annual< 1% wealth tax at a >$50M threshold<, with plans to go to $25M. It’s been introduced 3 years running. The one-time tax removes the constitutional barrier. Once that’s gone, the annual version becomes a much easier ballot measure. 🔃 CA Policy Center said: “If SEIU hopes to keep Medi-Cal spending growing, it may need to place repeated wealth taxes on the ballot—potentially lowering the threshold as billionaires flee.” The real risk for founders: At $1B, you’re taxing ~200 people. At $50M, you’re taxing 23,000 households—including most successful founders on paper before any liquidity event. The rational move isn’t to leave when you hit the threshold. It’s to leave—or never incorporate in CA—before you get anywhere close. ✈️ Net net: it will make sense to leave before the Series B. Vinod Khosla nailed it: “Even people who don’t expect this initiative to pass are still planning to leave because there will be another one.” The one-time tax is the constitutional Trojan horse. The annual tax — at a much lower threshold — is already waiting inside.

Stuff I've lost interest in as i got Older: - pro sports. faux tension - cars. who cares - fancy dinners. gout-in-waiting - fancy house. what's point Stuff I care more about: - helping others' careers - working with amazing CEOs - doing stuff truly at scale - family time

Just got back from 3 hours at Well Fargo. To reactivate a dormant bus account. I am tagged a VIP account and yet: - Supervisor had to approve everything - No wires over $100,000 - 5 days to clear a check - Told to “do it online instead” after 2 hours This is why SVB existed

If the CEO doesn't seem at least a little bit intense, Join a different start-up

Founders notice everything. Every bug, Every screwed up deal, Every employee that didn't give it their all, Everything every competitor does, Every moment that ever mattered. Everything that matters. Just make sure you keep most of it to yourself.

Don't send a resume to a CEO Send the CEO an email with 3 things you could own at their startup -- and how and why 10%-90% chance you get hired

Just got back from 3 hours at Well Fargo. To reactivate a dormant bus account. I am tagged a VIP account and yet: - Supervisor had to approve everything - No wires over $100,000 - 5 days to clear a check - Told to “do it online instead” after 2 hours This is why SVB existed

Today, Thiel, Sacks and Page prepare to leave California tomorrow. - Offices opened in Miami and Austin — today by Thiel - Driver’s Licenses Changed - Homes already owned California has approximately 255 billionaires — about a quarter of the U.S. total. The tax was estimated to raise $100B from ~200 of them. But as they scatter to Miami, Austin, and beyond, that number could shrink fast. It has already begun.

So this year I lost the most money I've ever lost on a VC investment It's OK. The fund will do OK. One loss can't kill a fund. But what the founder said still rattles in my brain: "What do you care? It's not mostly your money, anyway" A different world than I grew up in

My take on California’s “One-Time” Billionaire Tax. It’s much worse than it looks. 📉 Will it pass? Yes, likely. It only needs 50%+1 voter approval. SEIU + CTA have done this before—Prop 55 won 63% in 2016. ⚖️ Will it get tied up in litigation? Almost certainly. Retroactive wealth tax on a tax type CA has never had = due process challenges. Billionaires have the legal budgets for years of fights. 👋 But it’s clearly … only the start. The goal is an annual tax, not one-time. And the target is $25m-50m net worth folks, including illiquid foldings (early stage founders raising a Series B). The “one-time” framing is strategic, not terminal. The same coalition (CTA, CFT, SEIU) already has AB 259 written—an >annual< 1% wealth tax at a >$50M threshold<, with plans to go to $25M. It’s been introduced 3 years running. The one-time tax removes the constitutional barrier. Once that’s gone, the annual version becomes a much easier ballot measure. 🔃 CA Policy Center said: “If SEIU hopes to keep Medi-Cal spending growing, it may need to place repeated wealth taxes on the ballot—potentially lowering the threshold as billionaires flee.” The real risk for founders: At $1B, you’re taxing ~200 people. At $50M, you’re taxing 23,000 households—including most successful founders on paper before any liquidity event. The rational move isn’t to leave when you hit the threshold. It’s to leave—or never incorporate in CA—before you get anywhere close. ✈️ Net net: it will make sense to leave before the Series B. Vinod Khosla nailed it: “Even people who don’t expect this initiative to pass are still planning to leave because there will be another one.” The one-time tax is the constitutional Trojan horse. The annual tax — at a much lower threshold — is already waiting inside.

If we opened self-organized local SaaStr chapters and mini-events in different geographies, would you want to go? Would you want to manage one?

Thinking of a joining a startup for the first time? A quick guide on training and onboarding: 1-10 Employees: Nonexistent 11-20 Employees: Terrible 20-40 Employees: Some If worried, Then join something larger

Spouse teams don't work - Eventbrite Solo founders don't work - Zoom Need to move to SF - Shopify Winner takes all - Marketo Remind me the other rules again

The new CEO of Starbucks insisted on starting as a barista for 6 months He called together his inherited management team for an offsite None knew how to make an espresso

So far I've watched 3 VC seed deals this year where the founders just decided to keep the money for themselves and not build the product. All were on SAFEs, and they took the position they owed investors nothing and that in fact they were not even investors. Just SAFE holders. One eventually returned cash after keeping a large chunk for themselves. Another hired an attorney who said plainly nothing was owed to the investors and the founders could pay themselves whatever they wanted. I did not personally invest in these deals but I might have, they had a lot going for them (or so it seemed). This is going to happen in the Age of AI. It's the flip side of so many things also exploding so quickly and growing at insane rates. It's just a risk to be more aware of perhaps than in the past.

Had a seed investment acquired for $1B+ this month and ... lost money AMA

"Peter Thiel fired Elon Musk. Be -- he was kind about it. And he left Elon with all his economics (12% of PayPal). Be kind. He did what he had to do, but he was kind. And then Elon went back to Peter, and Founders Fund got to invest $20m to buy 10% of SpaceX. Perhaps the…

There clearly is a $500m consulting business TODAY in finishing folks' Replit and Loveable apps Maybe bigger

Did a demo today of the enterprise edition of a well known AI product Sales rep: - did not know what MCP is - had never heard of Claude but said "my guys will look into it" - said "your secret to being good at AI was really sick prompts" Then just threw a pricing slide up

SaaStr Annual Attendees, Sponsors & Speakers Rescheduled to SaaStr “Bi-Annual” in September 2020, SF Bay Area