What does it really take to build company culture from the ground up—especially when you’ve done it more than once? In this episode, Amir sits down with Darren Nix, founder and CEO of Steadily Insurance, to talk about the wins and missteps that come with building startups. Darren shares what’s stayed the same (and what hasn’t) across the four companies he’s founded, and why being deliberate about culture is more important than ever.
They get into how founders leave their fingerprints on everything—from hiring to habits—and why your company might accidentally turn into a copy of your employees’ old workplaces if you’re not paying attention. Whether you’re leading a 10-person team or scaling past 100, this episode is packed with hard-earned advice on keeping your culture intentional, honest, and real.
🧠 What You’ll Learn
Why the people you hire, fire, and promote say more about your culture than any value statement
How to avoid building a “Frankenstein culture” from your team’s past jobs
The role of founder intuition—and how it can still shape culture even as you scale
Why candor during hiring isn’t just refreshing—it saves time, trust, and turnover
What it means to find your “culture carriers” when you’re no longer in every interview
⏱ Highlights by Timestamp
00:00 – Intro to Darren & Steadily Insurance
01:29 – What’s the goal when building culture from scratch?
03:08 – The danger of not defining culture early
04:31 – Lessons from 4 startups (and what stuck)
07:10 – Founder imprint: how it changes with scale
09:45 – Why Darren rejected the “high-turnover sales model”
11:47 – Culture as habit: how norms are created (or missed)
13:30 – Transparency in hiring: a true story that worked
18:12 – Founder mode: when gut instincts outperform data
21:31 – “Culture carriers” and how to empower them
22:10 – A brilliant metaphor for why startups shouldn’t all look the same
💬 Quote to Remember
“Trying to do what everybody else does is almost by definition a recipe for an average outcome.” — Darren Nix
🎯 Practical Tips (If You’re a Founder or Manager)
