system > discipline

Day 471 | March 27, 2025 | Mission Bay, SF

📚 what I’m reading

1. the case against conversational interface (link)

2. how to ship like Beehiiv (link)

3. interview with Sam Altman and Ben Thompson (link)

🧠 system beats discipline

For the first year at Octolane, my morning routine was what I'd call "organized chaos." I'd wake up, grab my laptop before even brushing my teeth, and start putting out fires. My definition of breakfast became whatever snack was closest to my mousepad.

As our team grew, a painful truth emerged: everyone needed me more than I needed myself.

I became a human API endpoint. Constantly being pinged, processing requests, and returning responses until I crashed around midnight.

We were building research heavy products that demanded experimentation and risks on features that sometimes seemed too good to be true. My role morphed into keeping every engineer on track, running from office to office for endless customer feedback sessions, and iterating like our life depends on it.

I once did 7 in person customer calls in a single day in SF. By the end, I was introducing myself as "Hi, I'm Octolane, founder of One." The customer didn't even notice.

Despite everyone working seven days a week, our shipping timelines remained unpredictable, and projects kept stretching beyond horizons we could see.

After one particularly brutal missed deadline, my co-founder Rafi sat me down for a talk.

In that discussion, it clicked. We needed a system.

That night, we rebuilt everything from scratch.

We broke our weekly goals into daily tasks in Linear, with everyone posting their commitments in a #standup channel each morning. By 8:30 pm PST, you'd strike through what you finished. The satisfaction of crossing off tasks became our new dopamine hit.

We'd literally message each other "Struck through 3 tasks today! feeling like a BOSS!" as if we'd just climbed Everest. Our YC batchmates thought we were running a cult. They weren't entirely wrong.

Simple, visible, accountable. And somewhat addictive.

To maintain velocity, we implemented two non negotiable daily standups, each strictly capped at 15 minutes. Our first attempt lasted 47 minutes because apparently "non-negotiable" and "strictly capped" meant different things to different people. I started bringing an actual kitchen timer that made an unholy screaming sound when time was up. Problem solved.

As a remote company, this gave us the gift of seeing everyone twice daily and exchanging immediate feedback. Magic happened. Suddenly everyone knew what everyone else was doing. If someone fell behind or faced confusion, we'd all know within hours, not days.

The system created the discipline we desperately needed.

That system saved us. And probably saved my hairline too, though the gray hairs were already a lost cause.

what’s new?

1. New Headquarters Alert: We've moved to a sleek new office space on King Street (Tandem) – directly facing Oracle Park. Come say hi and enjoy the view of fly balls and tech dreams, both soaring over left field!

2. The Founder Schedule: 7-5 PM at my favorite cafe (breakfast, lunch, and customer feedback meetings, then to the office after rush hour for focused execution work. Turns out my best thinking happens over cappuccinos, not Zoom calls.

3. Octolane 3.0 Progress: Development is ahead of schedule and looking gorgeous! Your feedback shaped everything from the lightning fast search to the intuitive UX.

If you found value in this founder's journey or know someone building in AI who might, please share: https://www.coffeewithone.com/subscribe

Reply to this email with thoughts or questions - I read every response.