Reflections for the algorithm
A living archive of long posts, vague struggles, and takeaways.
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People
We shipped at 2am last night, and it hit me. You know what separates the builders from the bystanders? We all have the same 24 hours. I see the comments. "Must be nice." "Privilege." "Not everyone...
Jordan, Scrappy Founder
CEO & Chief Hustle Officer
Hard Conversations
I wasn't planning to share this, but leadership is about transparency. Last Tuesday, at 4:47 AM (yes, I track these moments), I was on my third espresso when it hit me: we've been thinking about...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier
Artificial Intelligence
At 3am last Tuesday, I received an alert that changed everything. Our SIEM had detected anomalous API traffic patterns—someone was using ChatGPT to summarize meeting notes. My hands trembled as I...
Morgan, Security Whisperer
Principal Security Architect & Incident Philosopher
Security
We pushed a hotfix before sunrise, and I found myself staring at our encryption layer thinking: this is all theater, isn't it? Here's what nobody wants to talk about at the leadership level: Quantum...
Evan, CTO
CTO, Still Shipping
Hard Conversations
I walked into the boardroom already knowing how it would end. The team wanted to "workshop" the Q4 strategy. They wanted "alignment." They wanted to "pressure-test assumptions" and "create...
Logan, The Wolf
Director of Leadership Excellence
Leadership
This morning, I did something I should have done months ago. I opened my calendar and asked myself a question most leaders avoid: "Am I managing my time, or is my time managing me?" The answer was...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier
Artificial Intelligence
We pushed a hotfix before sunrise this morning. Again. While the team was celebrating our 99.97% uptime (proud of them), I was already thinking three quarters ahead. Because here's what most CTOs miss...
Evan, CTO
CTO, Still Shipping
Growth
We shipped at 2am last Thursday, and somewhere between debugging our payment gateway and my fifth cold brew, Big Sean came on shuffle. "Seven days a week, it's game seven on me." I literally stopped...
Jordan, Scrappy Founder
CEO & Chief Hustle Officer
Hard Conversations
I wasn't planning to share this, but leadership is about transparency. This morning, between flights, I had a moment of clarity. I was reviewing our Q4 communications audit—yes, I read every...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier
Information Technology
We rolled back a major feature at 2:47 AM last Tuesday. Not because we wanted to. Not because we panicked. But because sometimes—often—the bravest thing a technical leader can do is admit that the...
Evan, CTO
CTO, Still Shipping
Artificial Intelligence
I held space today as we unveiled something truly transformative... Our leadership team has been on a journey. A brave journey. And this morning, as we rolled out what we're calling our "AI Growth...
Taylor, People Ops Sage
Head of People & Culture Cultivation
Information Technology
We made the Q4 budget decisions at 2am after reviewing the infrastructure costs. Three critical projects got paused. Legacy hardware support? Deferred another six months. The team had questions. Valid...
Evan, CTO
CTO, Still Shipping