Uploaded October 2025 | Updated September 2026, 2 weeks ago
Welcome to Founder Fridays - a Notion founder series - where we sit down with builders who’ve been in the trenches to talk shop - product, design, and the real lessons no one puts on a slide deck.
In this episode, Benjamin Paik, Co-founder of Afternoon.co (YC F24), joins Hilary Shirazi, Notion’s Head of Corp Dev, to share how he left Brex to tackle one of the least glamorous but most painful parts of startup life - back-office chaos. From building in a regulated space to leveraging AI for speed and scale, Ben breaks down what it takes to turn pain into product; and why most founders give up too soon.
To learn more about how Notion is supporting startups, please visit: https://ntn.so/founderfridays
Timestamps
00:00 Intro
01:57 Building Afternoon
05:57 Early Founder Shocks
07:38 YC Mindset Shift
09:22 AI and Accounting
12:26 Fundraising Lessons
14:26 Zero to One
17:19 The Tool Stack
19:20 Advice Block
Welcome to Founder Fridays - a Notion founder series - where we sit down with builders who’ve been in the trenches to talk shop - product, design, and the real lessons no one puts on a slide deck.
In this episode, Benjamin Paik, Co-founder of Afternoon.co (YC F24), joins Hilary Shirazi, Notion’s Head of Corp Dev, to share how he left Brex to tackle one of the least glamorous but most painful parts of startup life - back-office chaos. From building in a regulated space to leveraging AI for speed and scale, Ben breaks down what it takes to turn pain into product; and why most founders give up too soon.
To learn more about how Notion is supporting startups, please visit: https://ntn.so/founderfridays
Timestamps
00:00 Intro
01:57 Building Afternoon
05:57 Early Founder Shocks
07:38 YC Mindset Shift
09:22 AI and Accounting
12:26 Fundraising Lessons
14:26 Zero to One
17:19 The Tool Stack
19:20 Advice Block
