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
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
"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?
"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?
"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?
MG’s episode on @KnuckleUpHQ just dropped. Hear first hand on how @grinich has built and scaled WorkOS. Particularly love hearing about WorkOS’ org structure and his recruiting philosophy👇
"A week is 2% of the year. The cadence we operate on is: A week is not the shortest timeline. It's the longest timeline. What can we decide by tomorrow?" - @grinich.
Michael Grinich. Founder and CEO of WorkOS. The company powering the enterprise adoption of AI.
Knuckle Up ↓
--
00:00 Introduction
01:33 From design-obsessed founder to enterprise infrastructure
04:20 Michael’s year off and what made the WorkOS bet obvious
06:54 Why a great startup idea has to look bad first
09:46 Minimum awesome product beats MVP
11:09 The org with no CRO, no VP of sales, and one PM
13:29 Hiring for curiosity, not credentials
16:25 The "AI pilled" interview red flag
18:25 A week is 2% of the year
26:00 How WorkOS approaches brand
33:00 The future shape of engineering orgs
43:20 Why senior engineers benefit most from AI
44:45 Micro-leadership over micromanagement
49:10 Tough times in the early days
59:04 The reverse Peter principle
1:04:38 Quickfire: red flags, hires too early, and biggest fears
1:10:30 Michael's advice to his 25-year-old self
Hosted the second edition of wine night x ladies in tech x @AudaciousHQ at Verve on Fillmore last night. It was such a good time bringing together so many fun, accomplished women. The room was BUZZING! Already excited for the next one🍷
In my conversation with @bipulsinha, he shared his journey climbing his way back from one of the toughest phases of building Rubrik:
"I distinctly remember in 2019, I was driving back from work, and we had just missed two quarters in a row, and I started thinking that this is the company where I've put all my life, I'm not spending as much time with my family, I gave this everything and it is falling apart and I don't know why... I started crying. I had to stop the car on the side of the street...
And this was a very important moment where I realized that maybe I don't understand every aspect of this business. I don't have the command of the business because something bad is happening and I don't know what it is. And so I called two of my colleagues and we went back to the beginning of the company and looked at every deal we sold, every metric we generated, everything that we had ever done in the span of the next 2-3 weeks to really understand and come up with a thesis as what was happening, and that was really a transformational moment for the company."