Founding team @Hootsuite ($0 to $200m+ ARR). 3x founder. a16z Speedrun 006, building something new out of 180 Townsend Street...
San Francisco, CA
Joined June 2007
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I wish uber synched w/ my cal so that it could suggest a destination based on the time and where I need to go.
@andrewgordonmac 🙏
Greg Gunn retweeted
Me 1+ years later realizing the Perplexity CEO was completely full of shit.
"Perplexity CEO predicts AI could replace recruiters and assistants in as little as 6 months (Fast Company 7.21.25)"
Greg Gunn retweeted
I think you can buy tickets YouCanSeeEverything.movie
Greg Gunn retweeted
We just announced Canada’s new Productivity Mega Deduction.
This cuts Canada’s marginal effective tax rate from 13% to 6.4% on new business investment — the lowest of any major economy in the world.
Canada is building big — and becoming the best place in the world to build.
More here: pm.gc.ca/en/news/news-releas…
Greg Gunn retweeted
The name Lake Ontario comes from the Wendat word Ontari’io, which, appropriately, means “the lake is beautiful, the lake is big”.
The name is more than 400 years old, predating both the Confederation of Canada and the Declaration of Independence of the United States of America.
We know that America is changing. Their trading relationships, their foreign policies, their national monuments, their hydronyms.
Canadians also know that naming reality means calling it Lake Ontario – then, now and always.
Seriously VC Twitter…
You are using the r-word again?
Try harder to maintain your Kayfabe online persona without using language that punches down.
Do better.
Greg Gunn retweeted
more companies will be opening offices in canada
this is just the beginning
Greg Gunn retweeted
Offices that have recently opened up and/or are opening up in Toronto:
- OpenAI
- Harvey
- Decagon
- NVIDIA
- Opendoor
- Lyft
- EliseAI
- Zip
- Cognichip
Greg Gunn retweeted
Why Brian still obsesses over recruiting:
"Sam Altman (@sama) told me you're going to spend 50% of your time on hiring. I never did. It was my death blow.
As a leader, you can choose if you want to spend time hiring or managing. The more time you spend on recruiting, the less time you get to spend on management.
The first and last call I make every day is the recruiting team, still. I probably spend two, three hours on it every day.
The 2000s, I didn't. I thought it was all about having a recruiting machine, managing people. The great thing is I don't manage as much anymore because the really good people are self managing.
People should think about their first employee being a recruiter, not an engineer. Because they are the ones that get you every other person.
A company is as good as its people. The difference between the good companies and the great companies are the people."
My guest today is Brian Chesky (@bchesky), founder and CEO of Airbnb and one of the great consumer founders of the last 20 years.
Paul Graham coined "founder mode" based on Brian's experience running Airbnb. This conversation is about what comes after it, what he calls AI founder mode, and how it will force founders to focus even more on the details.
We talk about his eleven-star exercise for finding product market fit, why your first hire should be a recruiter, and why Airbnb's $100B IPO became one of the saddest days of his life.
Brian still comes across like the 17 year-old at the Rhode Island School of Design (RISD) who picked to study industrial design. His heroes are all artists. Da Vinci, Van Gogh, Walt Disney, and Steve Jobs, all of whom were working the week they died because they loved what they did.
Rick Rubin taught him that an artist is only an artist when they make things for themselves. Now Brian believes AI is the opportunity for all of us to do the same.
Enjoy!
Timestamps:
1:00 Studying Industrial Design
11:33 AI Founder Mode
17:02 Lack of Consumer AI Companies
22:10 Small Teams and Focused Problems
30:52 The Evolution from Founder to CEO
38:13 The 11-Star Experience
41:07 AI as a Canvas for Creativity
48:17 Detaching from Success
53:12 Founder-Led Moats
58:34 The Next Chapter of Airbnb
1:03:08 What Endures in the Age of AI
1:06:43 Lessons from Bodybuilding
1:10:20 The CEO's No. 1 Job
1:17:01 Activating Talent
1:20:39 The Kindest Thing
Greg Gunn retweeted
If you think AI replaces software engineers, here’s a quick thought experiment.
Imagine you’re a life sciences company. 10 years ago you want to invest heavily in lab automation, processing data at scale, and other software. You look at the cost of doing so and realize you can’t compete with tech for as many engineers as you need, so you pare down your goals and do what you can. Every new software project has a fixed cost of a certain sized team, so you can only do so much given budgets, ability to compete for talent, and other trade offs.
Now, AI comes along. And all of a sudden you have the *exact same* output tokens as the best tech companies in the world. Your engineers are using the same AI models as the tech industry, which means you have just boosted your engineering team by a some meaningful amount, while also neutralizing your differences with tech.
Do you continue with your pared down approach, or do you start to hire more engineers because each engineer is 2X or 5X more capable than before? In almost every company I’m talking to, they’re doing the latter.
Now extrapolate this to every bank, manufacturer, industrial company, retailer, and on and on. And extrapolate it not to just large enterprises, but also every SMB up and down the stack of these value chains. Oh, and also extrapolate this to other job functions, not just engineers. Resource scarce domains in marketing, legal, finance, design, and so on.
If you’re wondering why new jobs show up because of AI this is the reason. Any other view of what happens doesn’t contemplate the variety of unmet needs there are in the economy.
Greg Gunn retweeted
Jensen is one the smartest and most far seeing folks the world.
"If an AI scientist warns people that AI is going to permeate across radiology and radiologists are going to get wiped out, it might seem helpful but it's hurtful. If we convince everybody not to be radiologists and we now need radiologists, that actually is hurtful to society.
"It is hurtful to convince all the young college graduates not to study software engineering because we are going to need more software engineers than ever.
That's hurtful."
"Scaring people with nonsensical things, which are not going to happen, that this is an existential threat, there's a 20% chance that is is existential, that's ridiculous.
"That it's going to wipe out 50% of college level jobs.
"That is it going to completely destroy democracy.
"These kinds of comments are not helpful. They are made by...CEOS. And you become a CEO, maybe you adopt a God complex and somehow you know everything."
Brutal.
And right.
Greg Gunn retweeted
It’s wild to see how many of the best AI startups have added work trials as a key part of the hiring process.
When things are moving this fast, a candidate’s background on paper is often less relevant than what they can do with the tools in front of them.
Greg Gunn retweeted
🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦🇨🇦
30 of the 70 companies in our last @speedrun batch had founders born outside the US
and if we keep doing our job – and we will – that number is only going up:
* founders building products + teams internationally
* builders stuck in an H-1B job ready to accelerate their slope
* students here on F-1 who are ready to take a shot at their startup idea
Speedrun Global Founders is our answer >> our end-to-end approach to guiding founders through visas, customs, housing, banking, and building local SF community, while enabling founders from all over the globe to participate in Speedrun
we also have the coolest hat in venture - maybe thats a lame flex, but i honestly challenge you to show me better vc drip
you might catch a few of our founders wearing them today. come through Global Founders and I’ll bring you one 🫡
-apply below my friends-