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Hanging out tonight w @HubSpot’s Series A ($6mil pre$) and Series B ($24mil pre$) investors.
It worked out fine for all of us.
55.9K views
I got a chance to interview Jack Dorsey for the Long Strange Trip pod about his new article (in comments) on how to build a modern ai native company in 2026.
I took some of his ideas and mixed them with some observations about the hyper scaling ai native CEOs I work with every
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🔥 Top post: Dear founders, It's a good time to sell your company. Love, Br · 906.7K views
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I got a chance to interview Jack Dorsey for the Long Strange Trip pod about his new article (in comments) on how to build a modern ai native company in 2026.
I took some of his ideas and mixed them with some observations about the hyper s…
Dear Founders,
The vast majority of you are going to regret maximizing your valuation when the bubble pops. Just because you can raise at 100x, doesn't mean its the right decision.
♥️, Brian.
I've looked at a lot of AI startups recently at the app/agent layer. My take:
Everyone's building the same stuff.
Board meeting tips for CEO's of private companies:
1. Be transparent -- it builds trust. Board members can tell if you are spinning them. Save the sales pitch for the sales prospect.
2. Prep time -- Either send slides or a memo at leas…
Dear founders,
I have imposter syndrome too.
Love, Brian.
Dear Founders,
The CEO should captain/lead the vc pitch, regardless of how much experience the co-founder has.
Love,
Brian.
Dear Founders,
Take money off the table in the next round.
Love, Brian.
A founder asked me how he could develop thicker skin - more immunity to criticism. Any advice here for him?
The CEO’s of of the fastest growing startups are doing the following
1. 100% in office
2. Very very lean headcount
3. Mostly homegrown exec teams
4. Shooting for $1trillion. Unicorns are dead.
5. 80+ hour weeks
I wrote down literally everything I've learned about the journey from startup founder ($0) to scaleup CEO ($25billion). This thread is the on the lessons in LEADING. Several more threads coming on different topics.
I feel like the CEO playbook is being rewritten by Brian Chesky, Jensen Huang, and Elon Musk. I like where this is all heading.
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