Audacious Ventures

Seed stage VC leading $1-10M rounds. We focus on two jobs: 1/ Invest in force of nature founders; 2/ Help them recruit an A+ team. Then we get out of the way.

[Nakul Mandan @nakul]

When was it that @akothari and the @NotionHQ team knew that AI wasn't just a feature to add to the platform, they had to rethink the entire product?

[Nakul Mandan @nakul]

The way @akothari describes @NotionHQ, it feels like a craftsmen at work kinda place, built with a lot of thought and care.

My question back to him was: does the craftsmanship come at the cost of sheer operational intensity?

[Will Genesen @wgenesen]

Most seed founders think they have a channel problem. It's almost always a messaging problem.

Wrote up my playbook based on time at Ramp and OneSchema:

https://t.co/o8Z3zoKhwg

[Max Zang @maxzang305]

growth for dummies. 🔥 from @wgenesen

[Muzzammil Zaveri (MZ) @mzaveri]

hear @akothari give a masterclass on reinvention and rewiring in this AI era. a must-listen episode of knuckle up 🎧

[Nikunj Kothari @nikunj]

Every company needs a calm, steady yet enthusiastic hand at the wheel that helps the company fulfill its mission.

Most companies struggle to find this in the turbulent times we are in.

@akothari is this for @NotionHQ. Great chat that shares how he operates!

[Nakul Mandan @nakul]

"We were go-karting and doing quite well. Now we've moved to Formula 1, and we're in the middle of the pack. We have a shot at the podium but we have to rewire for the race we're in."

Akshay Kothari (@akothari). Cofounder and COO of @NotionHQ.

Three years from now, most pre-AI companies will be gone. Notion will be one of the few standing stronger than before. This episode is a field study in how they're pulling it off.

Knuckle Up ↓

00:00 Intro
01:27 What were Notion's core founding principles?
06:20 Which early cultural principles scaled, and which broke?
08:22 How did Notion hire its first employees, and where did they come from?
11:48 How does hiring work now that the founders can't meet everyone?
14:35 Why does Akshay, as COO, prefer to have zero direct reports?
19:05 How do Ivan, Simon, and Akshay divide the work?
21:07 Does Notion's intentionality ever conflict with speed?
25:25 What should other founders steal from Notion's culture?
28:11 When did AI become a reason to rethink the whole product?
30:44 Why were the early AI years a "swamp of despair"?
36:05 How do you push AI across a huge product without losing the user?
39:25 Does Notion buy its AI DNA or build it?
40:44 Should Notion be afraid of OpenAI, Anthropic, and fast copycats?
46:58 What's hardest about the reinvention, and what does "meet the LLM" mean?
52:42 Is Notion AI-native in every function yet?
54:36 Are Notion's engineers still writing code, and how has engineering changed?
1:01:07 Once building is cheap, what's the new bottleneck?
1:02:39 How is AI reshaping sales, marketing, and support?
1:09:07 How many agents run inside Notion, and who builds them?
1:11:28 How has recruiting changed for the AI era?
1:13:48 What still worries Akshay about Notion's future?
1:15:22 Quickfire: admired founders, books, overrated AI advice, and Akshay’s superpower
1:19:42 What should a $50M pre-AI company do in the next 90 days?

[Nakul Mandan @nakul]

Decagon has gone from 0 to 450 employees, & 0 to $4.5B of value in 3 years. When you're building at that pace in a competitive market, life is coming at you fast.

I asked @AshwinSreenivas how he is managing his psyche driving the company at this pace?

[Nakul Mandan @nakul]

.@DecagonAI has a 5 days in-person culture for everyone, and @AshwinSreenivas + @thejessezhang are in office 6 days a week.

I asked Ashwin: Why be so religious about the in-person culture? His answer ↓

[Nakul Mandan @nakul]

How @AshwinSreenivas and @DecagonAI maintain a high bar on recruiting while going from 0 to 450 employees in 3 years:

[Nakul Mandan @nakul]

The two types of FDEs according to @AshwinSreenivas, and why conflating the two can be dangerous for AI founders.

[Nakul Mandan @nakul]

"The pace of building has changed so quickly with AI. You have to give somewhere. And we gave for speed."

@AshwinSreenivas. Co-founder & President of @DecagonAI. You'd be hard pressed to find another startup moving as ferociously as this one.

Knuckle Up ↓

00:00 Intro
02:10 How did Jesse and Ashwin decide what to work on at Decagon?
04:19 Why did they reject the top-down market-sizing approach?
13:16 What does Decagon give up to keep moving fast?
17:54 6 days in-office for founders, 5 for everyone else.
23:33 Why didn't Decagon hire a single employee until $1M in ARR?
27:12 How do you hire 450 people in three years without compromising quality?
31:20 Are Decagon engineers even writing code anymore?
35:08 How does the IC engineer role change with Claude Code and Cursor?
36:32 How does EPD leadership change in the AI era?
40:15 Two types of FDE, and which one do most AI companies actually need?
49:21 How will the human role at Decagon evolve over three years?
57:15 Why is Decagon building its own models with Decagon Labs?
1:00:50 What worries Ashwin most about Decagon today?
1:03:52 How does Ashwin manage his psyche while running this fast?
1:08:00 Hiccups in the startup journey.
1:09:50 Quickfire: overrated advice, AI products, books, red flags
1:12:43 What would Ashwin tell his younger self about Decagon's journey?

[Muzzammil Zaveri (MZ) @mzaveri]

Great listen! Particularly love how @AshwinSreenivas distinguishes between two types of FDE work and the dangerous conflation as of late 👇

[Audacious Ventures @AudaciousHQ]

"We were maniacal about recruiting"

In this 3-min clip, @bipulsinha dropped several gems on recruiting:

- For a new startup, talent density is everything.
- Most founders delude themselves that they're hiring a top team. But they're not.
- In his first year of founding Rubrik, he spent 80% of his time recruiting!
- Created a pitch deck to pitch engineers, similar to a pitch deck for customers.
- How did he know he was recruiting top talent? He went after people who would ask him very, very hard questions.

[Nakul Mandan @nakul]

Why being a founder CEO requires an extreme growth mindset, according to @grinich.

[Nakul Mandan @nakul]

"We don't avoid micromanagement. It's not really a dirty word on our team." - @grinich

[Nakul Mandan @nakul]

"If you're a founder, almost by definition, you have to have a different opinion"

- @qasar on the need to be a contrarian....

Also watch for his hilarious opinion on the epidemic of group chats in silicon valley 🤣!

[Nakul Mandan @nakul]

"If you're just sitting around a table trying to come up with ideas and all you have available to you is like the internet, so does everybody else, right? And so you're not gonna have any like alpha in that, right? You have to find something that you have a unique insight." - @grinich

[Nakul Mandan @nakul]

We've all heard of Minimum Viable Product. What's Minimum Awesome Product? I asked @grinich.

[Nakul Mandan @nakul]

10 takes from my conversation with @grinich, founder of @WorkOS, on @KnuckleUpHQ:

1/ If everyone thinks your idea is good, it's a bad company to build. Too much consensus = too many competitors.

2/ Small TAM kills companies. There's no way to outrun it.

3/ Forget MVP. Ship a Minimum Awesome Product. With developers, your first impression is your brand forever.

4/ A week is 2% of the year. Stop saying "let's follow up next week."

5/ The era of the high-agency IC is now. Hiring "experts who've done it before" and turning the crank is not how scaling works.

6/ AI-native engineers? It's the bags under their eyes. Nights and weekends. If a CS candidate isn't writing code with AI, that's a red flag.

7/ Knowing what to build is the new bottleneck. Anyone can build anything fast now.

8/ Micro-leadership beats micromanagement, but only if leadership is doing more work than anyone else in the org. Micro-leadership is = manager has more context than the IC, explains the why.

9/ Culture is built around the customer and the product, not the offsite.

10/ "If you're the dinosaur, you don't know you're the dinosaur." Every founder I know should be asking themselves what they're holding onto from the pre-AI era.