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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

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.

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

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

CEOs should hold themselves to a higher standard Do not drink at work, do not drink at work events If you even suspect it's inappropriate, it is If someone tells something that makes them uncomfortable, change it. Today You are not an ordinary employee You are the CEO

First timer's guide to working directly with a CEO: 1. Meet your deadlines. 2. Be positive. 3. Raise your hand for help. 4. Be transparent and don't hide stuff. That is it.

You can't build a company on top of a Chrome plug-in See, e.g., Grammerly at $13B You can't build a company as a Gmail plug-in See, e.g., Calendly at $3B You can't build a company on top of Shopify See, e.g., Klaviyo at $9.5B

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

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

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

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

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

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.

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

There’s an AI Backlash happening now in the enterprise in particular Many vendors have promised big results and not delivering, especially in automation Promising to automate 50% of your contact center with AI, of your interactions with AI, etc. No one is hitting it The genie

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

So what if I told you about a SaaS company: - at $700m ARR - growing 30%+ - with 130% NRR - with 20%+ free cash margins - with no downturn and an epic brand - seeing 30%+ bookings next year, too what would that be worth? How about just $6.9 Billion. Barely 10x ARR It's a bit