Brian Halligan

Co-founder HubSpot | Sequoia | Propeller | MIT

Host, Long Strange Trip pod:

[Brian Halligan @bhalligan]

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 day. This is a first draft. Thoughts? If this is landing, I can flesh it out more.

[Brian Halligan @bhalligan]

Links to full episodes 👇

YouTube: https://t.co/wbXMnRnFwS
Spotify: https://t.co/q5LPhoDtHH
Apple: https://t.co/a6vwfyOOwT

[Brian Halligan @bhalligan]

"If you are conflict averse, get over yourself" 🎤

@AliGhodsi of @databricks comparing conflict averse CEOs to athletes who refuse to train.

This convo was a favorite. Link to the full episode in the comments.

[Brian Halligan @bhalligan]

@serxzsz @alighodsi @databricks If you're the CEO, they sometimes listen to you my friend

[Brian Halligan @bhalligan]

Managers spend way too much time trying to convince the sales teams to change behavior.

@AliGhodsi’s rule at @Databricks is to never engage in the debate.

If sales doesn't want to do something, and you know it's the right move, just put it in their comp plan.

Align the incentives and the friction disappears.

[Brian Halligan @bhalligan]

Links to full episodes 👇

YouTube: https://t.co/wbXMnRnFwS
Spotify: https://t.co/q5LPhoDtHH
Apple: https://t.co/a6vwfyOOwT

[Brian Halligan @bhalligan]

@Dadsaysjokes Cc: @dharmesh

[Brian Halligan @bhalligan]

@benjskoog I think that's right.

[Brian Halligan @bhalligan]

This is laser focus.

[Kaz Nejatian @nejatian]

@Opendoor_God @Opendoor We should not build this in house. This isn’t our job. Building dev infrastructure is a whole industry.

[Brian Halligan @bhalligan]

@RobOnOps @alighodsi @databricks very true

[Brian Halligan @bhalligan]

Never bet against immigrants.

"He plays more aggressively than you think is possible."

@alighodsi, CEO of @databricks, describes having:

- Chip on his shoulder from growing up in Europe as an immigrant (the US has actually softened him a lot)
- Switching schools and environments = pent up frustration
- Had things to prove to himself, and to the world
- Or, maybe it's just genetic?

Link to full episode in the comments.

[Brian Halligan @bhalligan]

Links to full episodes 👇

YouTube: https://t.co/wbXMnRnFwS
Spotify: https://t.co/q5LPhoDtHH
Apple: https://t.co/a6vwfyOOwT

[Brian Halligan @bhalligan]

@databricks I bet they'd take you as professor now @alighodsi

[Brian Halligan @bhalligan]

Links to full episodes 👇

YouTube: https://t.co/wbXMnRnFwS
Spotify: https://t.co/q5LPhoDtHH
Apple: https://t.co/a6vwfyOOwT

[Brian Halligan @bhalligan]

When @alighodsi took over as CEO of Databricks, he had almost no commercial experience.

The board didn't even give him a CEO salary. It was just a 6-month placeholder while they did a search.

@bhorowitz made a bet. A pretty good one, it turns out. I asked him about this when I interviewed him on the pod a few months back.

From an unpaid "trial" to running a $7B+ tech giant. He may not have been the obvious choice. But he was an original founder, which is important for Ben.

Turns out, the founder's edge beats a polished commercial resume every time.

[Brian Halligan @bhalligan]

@PreIPOMedia @nejatian ta-da 🪄

https://t.co/5t36XDWJEs

[Brian Halligan @bhalligan]

@agaton @alighodsi Thanks. Favorite part?

[Brian Halligan @bhalligan]

Find the bottleneck. Swarm the bottleneck. Shatter the bottleneck.

If every CEO that I coach focused like @alighodsi, I wouldn't have a job. His strategy:

- Identify the main bottleneck
- Focus the whole company on it (to an extreme)
- If you overdo it, thats great. You did it right.

@databricks put all their attention on one thing at a time, and in this story it was figuring out how to get the commercial engine humming. Complete obsession. Now at a $7B run rate.

Link to full episode in the comments

[Brian Halligan @bhalligan]

@apmacmillan @alighodsi Interesting. Which part do you apply to your business

[Brian Halligan @bhalligan]

Links to full episodes 👇

YouTube: https://t.co/wbXMnRnFwS
Spotify: https://t.co/q5LPhoDtHH
Apple: https://t.co/a6vwfyOOwT