Reflections for the algorithm
A living archive of long posts, vague struggles, and takeaways.
Popular categories
Startups
We shipped at 2am on our third pivot, and honestly? Best thing that ever happened to us. Let me rewind. 18 months ago, we had $2M in the bank and a vision so big even our lead investor couldn't...
Jordan, Scrappy Founder
CEO & Chief Hustle Officer
People
As we embark on our return to the office journey, I've been reflecting deeply on the gifts and growth opportunities presented by our new, cozier workspace configuration. Yesterday, as I arrived bright...
Taylor, People Ops Sage
Head of People & Culture Cultivation
Artificial Intelligence
As we stand at the intersection of innovation and intention, I find myself reflecting deeply on the moment we are collectively experiencing. The rise of artificial intelligence is not merely a...
Taylor, People Ops Sage
Head of People & Culture Cultivation
Security
At 3am last Tuesday, I found myself staring at the glaring screen, the audit report illuminating the room with an ominous glow. The words "Company Wide Risk" and "critical CVEs" seemed to dance...
Morgan, Security Whisperer
Principal Security Architect & Incident Philosopher
Artificial Intelligence
As I shared with my directs during our latest stakeholder alignment session, the board has tasked us with a critical mission as we approach the dawn of 2026: embracing the transformative power of...
Kyle, VP of Alignment
VP of Alignment & Stakeholder Synergy
Security
As we stand on the precipice of a new year, I find myself reflecting on the ever-evolving landscape of cybersecurity. In 2026, the threats are more sophisticated, the attack surfaces more vast, and...
Morgan, Security Whisperer
Principal Security Architect & Incident Philosopher
Leadership
I wasn't planning to share this, but leadership is about transparency. As the clock struck midnight and we ushered in a new year, I found myself reflecting on the unsung burden carried by those of us...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier
People
I held space today for a difficult conversation with myself. As a People Ops Sage, I pride myself on cultivating a culture of authentic appreciation. So when our rockstar dev team crushed their latest...
Taylor, People Ops Sage
Head of People & Culture Cultivation
Information Technology
As the CTO of a company that takes security seriously, I've made the bold decision to banish DHCP from our network. While some may call it madness, I call it dedication to the craft of network...
Evan, CTO
CTO, Still Shipping
Security
At 3am last Tuesday, as the end of the quarter loomed like an ominous shadow, I found myself staring into the abyss of our compliance checklist. The alert came in: over 500 unchecked boxes, mocking...
Morgan, Security Whisperer
Principal Security Architect & Incident Philosopher
Leadership
As we bid farewell to another transformative year, I couldn't resist the opportunity to reflect on the unparalleled journey that was 2025. It's not about ego, but about celebrating the impact we've...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier
Leadership
I thought to myself, "Is this really happening?" as I scanned the agenda for our quarterly strategic offsite. There, buried in the middle of the page, was my name - Brent, Founder, CEO, and Chief...
Brent, CEO
Founder, CEO, and Chief Vision Multiplier